Heterocyclic compound and organic light emitting element comprising same

ABSTRACT

The present specification relates to a heterocyclic compound represented by Chemical Formula 1, and an organic light emitting device comprising the same.

TECHNICAL FIELD

The present specification relates to a heterocyclic compound and anorganic light emitting device comprising the same.

BACKGROUND ART

An electroluminescent device is one type of self-emissive displaydevices, and has an advantage of having a wide viewing angle, and a highresponse speed as well as having an excellent contrast.

An organic light emitting device has a structure disposing an organicthin film between two electrodes. When a voltage is applied to anorganic light emitting device having such a structure, electrons andholes injected from the two electrodes bind and pair in the organic thinfilm, and light emits as these annihilate. The organic thin film may beformed in a single layer or a multilayer as necessary.

A material of the organic thin film may have a light emitting functionas necessary. For example, as a material of the organic thin film,compounds capable of forming a light emitting layer themselves alone maybe used, or compounds capable of performing a role of a host or a dopantof a host-dopant-based light emitting layer may also be used. Inaddition thereto, compounds capable of performing roles of holeinjection, hole transfer, electron blocking, hole blocking, electrontransfer, electron injection and the like may also be used as a materialof the organic thin film.

Development of an organic thin film material has been continuouslyrequired for enhancing performance, lifetime or efficiency of an organiclight emitting device.

DISCLOSURE Technical Problem

The present disclosure is directed to providing a novel heterocycliccompound and an organic light emitting device comprising the same.

Technical Solution

One embodiment of the present application provides a heterocycliccompound represented by the following Chemical Formula 1.

In Chemical Formula 1,

R₂ to R₅ are the same as or different from each other, and eachindependently selected from the group consisting of hydrogen; deuterium;a halogen group; —CN; a substituted or unsubstituted alkyl group; asubstituted or unsubstituted alkenyl group; a substituted orunsubstituted alkynyl group; a substituted or unsubstituted alkoxygroup; a substituted or unsubstituted cycloalkyl group; a substituted orunsubstituted heterocycloalkyl group; a substituted or unsubstitutedaryl group; a substituted or unsubstituted heteroaryl group; —SiRR′R″;—P(═O)RR′; and an amine group unsubstituted or substituted with asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedaryl group, or a substituted or unsubstituted heteroaryl group, or twoor more groups adjacent to each other bond to each other to form asubstituted or unsubstituted aliphatic or aromatic hydrocarbon ring,

Ra is hydrogen; a substituted or unsubstituted alkyl group; asubstituted or unsubstituted aryl group; or a substituted orunsubstituted heteroaryl group,

Ar₁ is represented by -(L1)p-(Z1)q,

Ar₂ is represented by -(L2)r-(Z2)s,

L1 and L2 are the same as or different from each other, and eachindependently a substituted or unsubstituted arylene group; or asubstituted or unsubstituted heteroarylene group,

Z1 and Z2 are the same as or different from each other, and eachindependently selected form the group consisting of deuterium; a halogengroup; —CN; a substituted or unsubstituted alkyl group; a substituted orunsubstituted alkenyl group; a substituted or unsubstituted alkynylgroup; a substituted or unsubstituted alkoxy group; a substituted orunsubstituted cycloalkyl group; a substituted or unsubstitutedheterocycloalkyl group; a substituted or unsubstituted aryl group; asubstituted or unsubstituted heteroaryl group; —SiRR′R″; —P(═O)RR′; andan amine group unsubstituted or substituted with a substituted orunsubstituted alkyl group, a substituted or unsubstituted aryl group, ora substituted or unsubstituted heteroaryl group,

R, R′ and R″ are the same as or different from each other, and eachindependently hydrogen; deuterium; —CN; a substituted or unsubstitutedalkyl group; a substituted or unsubstituted cycloalkyl group; asubstituted or unsubstituted aryl group; or a substituted orunsubstituted heteroaryl group,

p and r are an integer of 1 to 4,

q and s are an integer of 1 to 3, and

n is an integer of 0 to 4.

Another embodiment of the present application provides an organic lightemitting device comprising a first electrode; a second electrodeprovided opposite to the first electrode; and one or more organicmaterial layers provided between the first electrode and the secondelectrode, wherein one or more layers of the organic material layerscomprise the heterocyclic compound according to one embodiment of thepresent application.

Advantageous Effects

The compound described in the present specification can be used as anorganic material layer material of an organic light emitting device. Thecompound is capable of performing a role of a hole injection material, ahole transfer material, a light emitting material, an electron transfermaterial, an electron injection material and the like in the organiclight emitting device. Particularly, the compound can be used as anelectron transfer layer material, a hole blocking layer material or acharge generation layer material of the organic light emitting device.

Specifically, when using the compound represented by Chemical Formula 1in the organic material layer, a driving voltage is lowered and lightefficiency is enhanced in the device, and device lifetime properties canbe enhanced by thermal stability of the compound.

DESCRIPTION OF DRAWINGS

FIG. 1 to FIG. 4 are diagrams each schematically illustrating alamination structure of an organic light emitting device according toone embodiment of the present application.

REFERENCE NUMERAL

-   -   100: Substrate    -   200: Anode    -   300: Organic Material Layer    -   301: Hole Injection Layer    -   302: Hole Transfer Layer    -   303: Light Emitting Layer    -   304: Hole Blocking Layer    -   305: Electron Transfer Layer    -   306: Electron Injection Layer    -   400: Cathode

MODE FOR DISCLOSURE

Hereinafter, the present application will be described in detail.

The term “substituted” means a hydrogen atom bonding to a carbon atom ofa compound is changed to another substituent, and the position ofsubstitution is not limited as long as it is a position at which thehydrogen atom is substituted, that is, a position at which a substituentcan substitute, and when two or more substituents substitute, the two ormore substituents may be the same as or different from each other.

In the present specification, the halogen may be fluorine, chlorine,bromine or iodine.

In the present specification, the alkyl group comprises linear orbranched having 1 to 60 carbon atoms, and may be further substitutedwith other substituents. The number of carbon atoms of the alkyl groupmay be from 1 to 60, specifically from 1 to 40 and more specificallyfrom 1 to 20. Specific examples thereof may comprise a methyl group, anethyl group, a propyl group, an n-propyl group, an isopropyl group, abutyl group, an n-butyl group, an isobutyl group, a tert-butyl group, asec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentylgroup, an n-pentyl group, an isopentyl group, a neopentyl group, atert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentylgroup, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, ann-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, acyclohexylmethyl group, an octyl group, an n-octyl group, a tert-octylgroup, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentylgroup, an n-nonyl group, a 2,2-dimethylheptyl group, a 1-ethyl-propylgroup, a 1,1-dimethyl-propyl group, an isohexyl group, a 2-methylpentylgroup, a 4-methylhexyl group, a 5-methylhexyl group and the like, butare not limited thereto.

In the present specification, the alkenyl group comprises linear orbranched having 2 to 60 carbon atoms, and may be further substitutedwith other substituents. The number of carbon atoms of the alkenyl groupmay be from 2 to 60, specifically from 2 to 40 and more specificallyfrom 2 to 20. Specific examples thereof may comprise a vinyl group, a1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenylgroup, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, anallyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-ylgroup, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, astyrenyl group and the like, but are not limited thereto.

In the present specification, the alkynyl group comprises linear orbranched having 2 to 60 carbon atoms, and may be further substitutedwith other substituents. The number of carbon atoms of the alkynyl groupmay be from 2 to 60, specifically from 2 to 40 and more specificallyfrom 2 to 20.

In the present specification, the alkoxy group may be linear, branchedor cyclic. The number of carbon atoms of the alkoxy group is notparticularly limited, but is preferably from 1 to 20. Specific examplesthereof may comprise methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy,isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy,isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy,n-octyloxy, n-nonyloxy, n-decyloxy, benxyloxy, p-methylbenzyloxy and thelike, but are not limited thereto.

In the present specification, the cycloalkyl group comprises monocyclicor multicyclic having 3 to 60 carbon atoms, and may be furthersubstituted with other substituents. Herein, the multicyclic means agroup in which the cycloalkyl group is directly linked to or fused withother cyclic groups. Herein, the other cyclic groups may be a cycloalkylgroup, but may also be different types of cyclic groups such as aheterocycloalkyl group, an aryl group and a heteroaryl group. The numberof carbon groups of the cycloalkyl group may be from 3 to 60,specifically from 3 to 40 and more specifically from 5 to 20. Specificexamples thereof may comprise a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a 3-methylcyclopentyl group, a2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexylgroup, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, acycloheptyl group, a cyclooctyl group and the like, but are not limitedthereto.

In the present specification, the heterocycloalkyl group comprises O, S,Se, N or Si as a heteroatom, comprises monocyclic or multicyclic having2 to 60 carbon atoms, and may be further substituted with othersubstituents. Herein, the multicyclic means a group in which theheterocycloalkyl group is directly linked to or fused with other cyclicgroups. Herein, the other cyclic groups may be a heterocycloalkyl group,but may also be different types of cyclic groups such as a cycloalkylgroup, an aryl group and a heteroaryl group. The number of carbon atomsof the heterocycloalkyl group may be from 2 to 60, specifically from 2to 40 and more specifically from 3 to 20.

In the present specification, the aryl group comprises monocyclic ormulticyclic having 6 to 60 carbon atoms, and may be further substitutedwith other substituents. Herein, the multicyclic means a group in whichthe aryl group is directly linked to or fused with other cyclic groups.Herein, the other cyclic groups may be an aryl group, but may also bedifferent types of cyclic groups such as a cycloalkyl group, aheterocycloalkyl group and a heteroaryl group. The aryl group comprisesa spiro group. The number of carbon atoms of the aryl group may be from6 to 60, specifically from 6 to 40 and more specifically from 6 to 25.Specific examples of the aryl group may comprise a phenyl group, abiphenyl group, a triphenyl group, a naphthyl group, an anthryl group, achrysenyl group, a phenanthrenyl group, a perylenyl group, afluoranthenyl group, a triphenylenyl group, a phenalenyl group, apyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenylgroup, an indenyl group, an acenaphthylenyl group, a benzofluorenylgroup, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, a fusedring thereof, and the like, but are not limited thereto.

In the present specification, the silyl group is a substituentcomprising Si, having the Si atom directly linked as a radical, and isrepresented by —SiR₁₀₄R₁₀₅R₁₀₆. R₁₀₄ to R₁₀₆ are the same as ordifferent from each other, and may be each independently a substituentformed with at least one of hydrogen; deuterium; a halogen group; analkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; anaryl group; and a heterocyclic group. Specific examples of the silylgroup may comprise a trimethylsilyl group, a triethylsilyl group, at-butyldimethylsilyl group, a vinyldimethylsilyl group, apropyldimethylsilyl group, a triphenylsilyl group, a diphenylsilylgroup, a phenylsilyl group and the like, but are not limited thereto.

In the present specification, the fluorenyl group may be substituted,and adjacent substituents may bond to each other to form a ring.

When the fluorenyl group is substituted,

and the like may be included. However, the structure is not limitedthereto.

In the present specification, the heteroaryl group comprises O, S, Se, Nor Si as a heteroatom, comprises monocyclic or multicyclic having 2 to60 carbon atoms, and may be further substituted with other substituents.Herein, the multicyclic means a group in which the heteroaryl group isdirectly linked to or fused with other cyclic groups. Herein, the othercyclic groups may be a heteroaryl group, but may also be different typesof cyclic groups such as a cycloalkyl group, a heterocycloalkyl groupand an aryl group. The number of carbon atoms of the heteroaryl groupmay be from 2 to 60, specifically from 2 to 40 and more specificallyfrom 3 to 25. Specific examples of the heteroaryl group may comprise apyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group,a furanyl group, a thiophene group, an imidazolyl group, a pyrazolylgroup, an oxazolyl group, an isoxazolyl group, a thiazolyl group, anisothiazolyl group, a triazolyl group, a furazanyl group, an oxadiazolylgroup, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, apyranyl group, a thiopyranyl group, a diazinyl group, an oxazinyl group,a thiazinyl group, a dioxynyl group, a triazinyl group, a tetrazinylgroup, a quinolyl group, an isoquinolyl group, a quinazolinyl group, anisoquinazolinyl group, a quinozolinyl group, a naphthyridyl group, anacridinyl group, a phenanthridinyl group, an imidazopyridinyl group, adiazanaphthalenyl group, a triazaindene group, an indolyl group, anindolizinyl group, a benzothiazolyl group, a benzoxazolyl group, abenzimidazolyl group, a benzothiophene group, a benzofuran group, adibenzothiophene group, a dibenzofuran group, a carbazolyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a phenazinyl group, adibenzosilole group, spirobi(dibenzosilole), a dihydrophenazinyl group,a phenoxazinyl group, a phenanthridyl group, an imidazopyridinyl group,a thienyl group, an indolo[2,3-a]carbazolyl group, anindolo[2,3-b]carbazolyl group, an indolinyl group, a10,11-dihydro-dibenzo[b,f]azepine group, a 9,10-dihydroacridinyl group,a phenanthrazinyl group, a phenothiathiazinyl group, a phthalazinylgroup, a naphthylidinyl group, a phenanthrolinyl group, abenzo[c][1,2,5]thiadiazolyl group, a5,10-dihydrobenzo[b,e][1,4]azasilinyl, a pyrazolo[1,5-c]quinazolinylgroup, a pyrido[1,2-b]indazolyl group, apyrido[1,2-a]imidazo[1,2-e]indolinyl group, a5,11-dihydroindeno[1,2-b]carbazolyl group and the like, but are notlimited thereto.

In the present specification, the amine group may be selected from thegroup consisting of a monoalkylamine group; a monoarylamine group; amonoheteroarylamine group; —NH₂; a dialkylamine group; a diarylaminegroup; a diheteroarylamine group; an alkylarylamine group; analkylheteroarylamine group; and an arylheteroarylamine group, andalthough not particularly limited thereto, the number of carbon atoms ispreferably from 1 to 30. Specific examples of the amine group maycomprise a methylamine group, a dimethylamine group, an ethylaminegroup, a diethylamine group, a phenylamine group, a naphthylamine group,a biphenylamine group, a dibiphenylamine group, an anthracenylaminegroup, a 9-methyl-anthracenylamine group, a diphenylamine group, aphenylnaphthylamine group, a ditolylamine group, a phenyltolylaminegroup, a triphenylamine group, a biphenylnaphthylamine group, aphenylbiphenylamine group, a biphenylfluorenylamine group, aphenyltriphenylenylamine group, a biphenyltriphenylenylamine group andthe like, but are not limited thereto.

In the present specification, the arylene group means the aryl grouphaving two bonding sites, that is, a divalent group. Descriptions on thearyl group provided above may be applied thereto except for each being adivalent. In addition, the heteroarylene group means the heteroarylgroup having two bonding sites, that is, a divalent group. Descriptionson the heteroaryl group provided above may be applied thereto except foreach being a divalent.

In the present specification, specific examples of the phosphine oxidegroup may comprise a diphenylphosphine oxide group, adinaphthylphosphine oxide group and the like, but are not limitedthereto.

In the present specification, an “adjacent” group may mean a substituentsubstituting an atom directly linked to an atom substituted by thecorresponding substituent, a substituent sterically most closelypositioned to the corresponding substituent, or another substituentsubstituting an atom substituted by the corresponding substituent. Forexample, two substituents substituting ortho positions in a benzenering, and two substituents substituting the same carbon in an aliphaticring may be interpreted as groups “adjacent” to each other.

In the present specification, the term “substituted” means a hydrogenatom bonding to a carbon atom of a compound is changed to anothersubstituent, and the position of substitution is not limited as long asit is a position at which the hydrogen atom is substituted, that is, aposition at which a substituent can substitute, and when two or moresubstituents substitute, the two or more substituents may be the same asor different from each other.

In the present specification, “substituted or unsubstituted” means beingsubstituted with one or more substituents selected from the groupconsisting of C1 to C60 linear or branched alkyl; C2 to C60 linear orbranched alkenyl; C2 to C60 linear or branched alkynyl; C3 to C60monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclicheterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60monocyclic or polycyclic heteroaryl; —SiRR′R″; —P(═O)RR′; C1 to C20alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and C2 to C60monocyclic or polycyclic heteroarylamine, or being unsubstituted, orbeing substituted with a substituent linking two or more substituentsselected from among the substituents illustrated above, or beingunsubstituted.

One embodiment of the present application provides a compoundrepresented by Chemical Formula 1.

Chemical Formula 1 has a structure of a quinoline group being fused toan indole group, and when having an indole group, Chemical Formula 1 hasa sp3 unshared electron pair instead of a sp2 unshared electron pair inthe structure. Accordingly, hole transfer properties are particularlysuperior compared to when having benzothiophene or benzofuran with a sp2noncovalent bond. This affects exciton formation in a light emittinglayer when used as an organic material layer of an organic lightemitting device afterword resulting in an increase in the deviceefficiency and lifetime.

In one embodiment of the present application, R₂ to R₅ of ChemicalFormula 1 are the same as or different from each other, and may be eachindependently selected from the group consisting of hydrogen; deuterium;a halogen group; —CN; a substituted or unsubstituted alkyl group; asubstituted or unsubstituted alkenyl group; a substituted orunsubstituted alkynyl group; a substituted or unsubstituted alkoxygroup; a substituted or unsubstituted cycloalkyl group; a substituted orunsubstituted heterocycloalkyl group; a substituted or unsubstitutedaryl group; a substituted or unsubstituted heteroaryl group; —SiRR′R″;—P(═O)RR′; and an amine group unsubstituted or substituted with asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedaryl group, or a substituted or unsubstituted heteroaryl group, or twoor more groups adjacent to each other may bond to each other to form asubstituted or unsubstituted aliphatic or aromatic hydrocarbon ring.

In another embodiment, R₂ to R₅ of Chemical Formula 1 are the same as ordifferent from each other, and may be each independently selected fromthe group consisting of hydrogen; a substituted or unsubstituted C1 toC60 aryl group; and a substituted or unsubstituted C2 to C60 heteroarylgroup, or two or more groups adjacent to each other may bond to eachother to form a substituted or unsubstituted aromatic hydrocarbon ring.

In another embodiment, R₂ to R₅ of Chemical Formula 1 are the same as ordifferent from each other, and may be each independently hydrogen, ortwo or more groups adjacent to each other may bond to each other to forma substituted or unsubstituted C2 to C60 aromatic hydrocarbon ring.

In another embodiment, R₂ to R₅ of Chemical Formula 1 are the same as ordifferent from each other, and may be each independently hydrogen, ortwo or more groups adjacent to each other may bond to each other to forma C2 to C40 aromatic hydrocarbon ring.

In another embodiment, R₂ to R₅ of Chemical Formula 1 are the same as ordifferent from each other, and may be each independently hydrogen, ortwo or more groups adjacent to each other may bond to each other to forma benzene ring.

In one embodiment of the present application, R₂ and R₃ among R₂ to R₅of Chemical Formula 1 bond to each other to form a benzene ring, and therest may be hydrogen.

In one embodiment of the present application, R₃ and R₄ among R₂ to R₅of Chemical Formula 1 bond to each other to form a benzene ring, and therest may be hydrogen.

In one embodiment of the present application, R₄ and R₅ among R₂ to R₅of Chemical Formula 1 bond to each other to form a benzene ring, and therest may be hydrogen.

In one embodiment of the present application, Ra of Chemical Formula 1may be hydrogen; a substituted or unsubstituted alkyl group; asubstituted or unsubstituted aryl group; or a substituted orunsubstituted heteroaryl group.

In another embodiment, Ra of Chemical Formula 1 may be hydrogen; asubstituted or unsubstituted C6 to C60 aryl group; or a substituted orunsubstituted C2 to C60 heteroaryl group.

In another embodiment, Ra of Chemical Formula 1 may be hydrogen; a C6 toC40 aryl group; or a C2 to C40 heteroaryl group.

In another embodiment, Ra of Chemical Formula 1 may be hydrogen.

In one embodiment of the present application, Ar₁ may be represented by-(L1)p-(Z1)q, and Ar₂ may be represented by -(L2)r-(Z2)s.

By Ar₁ and Ar₂ of Chemical Formula 1 of the present application beingsubstituted with each substituent, thermal stability is superiorcompared to when single substituted, and structurally, indole-structuredsubstituents controlling hole transfer properties may be introduced morediversely compared to when single substituted, and controllingstructural properties may be superior.

In one embodiment of the present application, L1 and L2 are the same asor different from each other, and may be each independently asubstituted or unsubstituted arylene group; or a substituted orunsubstituted heteroarylene group.

In another embodiment, L1 and L2 are the same as or different from eachother, and may be each independently a substituted or unsubstituted C6to C60 arylene group; or a substituted or unsubstituted C2 to C60heteroarylene group.

In another embodiment, L1 and L2 are the same as or different from eachother, and may be each independently a C6 to C40 arylene group; or a C2to C40 heteroarylene group.

In another embodiment, L1 and L2 are the same as or different from eachother, and may be each independently a C6 to C40 arylene group; or a C2to C40 heteroarylene group.

In another embodiment, L1 and L2 are the same as or different from eachother, and may be each independently a phenylene group; a biphenylenegroup; a naphthalene group; a phenanthrenylene group; a triphenylenylenegroup; a fluoranthenylene group; a pyrenylene group; a divalent pyridinegroup; a divalent pyrimidine group; or a divalent triazine group.

In one embodiment of the present application, L1 may be a substituted orunsubstituted C6 to C60 arylene group; or a substituted or unsubstitutedC2 to C60 heteroarylene group.

In another embodiment, L1 may be a substituted or unsubstituted C6 toC40 arylene group; or a substituted or unsubstituted C2 to C40heteroarylene group.

In another embodiment, L1 may be a C6 to C40 arylene group; or a C2 toC40 heteroarylene group.

In another embodiment, L1 may be a phenylene group; a biphenylene group;a naphthalene group; a phenanthrenylene group; a divalent pyridinegroup; a divalent pyrimidine group; or a divalent triazine group.

In one embodiment of the present application, L2 may be a substituted orunsubstituted C6 to C60 arylene group; or a substituted or unsubstitutedC2 to C60 heteroarylene group.

In another embodiment, L2 may be a substituted or unsubstituted C6 toC40 arylene group; or a substituted or unsubstituted C2 to C40heteroarylene group.

In another embodiment, L2 may be a C6 to C40 arylene group; or a C2 toC40 heteroarylene group.

In another embodiment, L2 may be a phenylene group; a biphenylene group;a naphthalene group; a phenanthrenylene group; a triphenylenylene group;a fluoranthenylene group; a pyrenylene group; a divalent pyridine group;a divalent pyrimidine group; or a divalent triazine group.

In one embodiment of the present application, Z1 and Z2 are the same asor different from each other, and may be each independently selectedfrom the group consisting of hydrogen; deuterium; a halogen group; —CN;a substituted or unsubstituted alkyl group; a substituted orunsubstituted alkenyl group; a substituted or unsubstituted alkynylgroup; a substituted or unsubstituted alkoxy group; a substituted orunsubstituted cycloalkyl group; a substituted or unsubstitutedheterocycloalkyl group; a substituted or unsubstituted aryl group; asubstituted or unsubstituted heteroaryl group; —SiRR′R″; —P(═O)RR′; andan amine group unsubstituted or substituted with a substituted orunsubstituted alkyl group, a substituted or unsubstituted aryl group, ora substituted or unsubstituted heteroaryl group.

In another embodiment, Z1 and Z2 are the same as or different from eachother, and may be each independently hydrogen; a substituted orunsubstituted aryl group; a substituted or unsubstituted heteroarylgroup; or P(═O)RR′.

In another embodiment, Z1 and Z2 are the same as or different from eachother, and may be each independently hydrogen; a substituted orunsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 toC60 heteroaryl group; or P(═O)RR′.

In another embodiment, Z1 and Z2 are the same as or different from eachother, and may be each independently hydrogen; a substituted orunsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 toC40 heteroaryl group; or P(═O)RR′.

In another embodiment, Z1 and Z2 are the same as or different from eachother, and may be each independently hydrogen; a C6 to C40 aryl groupunsubstituted or substituted with one or more substituents selected fromthe group consisting of a C6 to C40 aryl group, a C2 to C40 heteroarylgroup, a C1 to C40 alkyl group and —CN; a C2 to C40 heteroaryl groupunsubstituted or substituted with a C6 to C40 aryl group; or P(═O)RR′,and the substituent may be unsubstituted or substituted again with a C1to C40 alkyl group; or a C6 to C40 aryl group.

In another embodiment, Z1 and Z2 are the same as or different from eachother, and may be each independently hydrogen; P(═O)RR′; a phenyl groupunsubstituted or substituted with one or more substituents selected fromthe group consisting of a 9,9′-dimethylfluorene group, —CN, atriphenylene group, a phenanthrene group, a phenyl group, a dibenzofurangroup and a dibenzothiophene group; a phenyl group unsubstituted orsubstituted with a carbazole group unsubstituted or substituted with aphenyl group; a biphenyl group; a triphenylene group; a fluorene groupunsubstituted or substituted with a methyl group; a phenanthrene group;a spirofluorene group; a pyridine group; a carbazole group; adibenzofuran group; a dibenzothiophene group; or a phenanthroline groupunsubstituted or substituted with a phenyl group.

In one embodiment of the present application, Z1 may be hydrogen;P(═O)RR′; a phenyl group unsubstituted or substituted with one or moresubstituents selected from the group consisting of a carbazole groupunsubstituted or substituted with a phenyl group, a dibenzofuran groupand a dibenzothiophene group; a biphenyl group; a spirobifluorene group;a fluorene group unsubstituted or substituted with a methyl group; apyridine group; a dibenzofuran group; a dibenzothiophene group; or aphenanthroline group unsubstituted or substituted with a phenyl group.

In one embodiment of the present application, Z2 may be hydrogen;P(═O)RR′; a phenyl group unsubstituted or substituted with one or moresubstituents selected from the group consisting of a phenyl group, aphenanthrene group, a triphenylene group, —CN, a 9,9′-dimethylfluorenegroup, a carbazole group and a dibenzofuran group; a biphenyl group; atriphenylene group; a fluorene group unsubstituted or substituted with amethyl group; a phenanthrene group; a pyridine group; a carbazole group;or a dibenzofuran group.

In one embodiment of the present application, R, R′ and R″ are the sameas or different from each other, and may be each independently hydrogen;deuterium; —CN; a substituted or unsubstituted alkyl group; asubstituted or unsubstituted cycloalkyl group; a substituted orunsubstituted aryl group; or a substituted or unsubstituted heteroarylgroup.

In another embodiment, R, R′ and R″ are the same as or different fromeach other, and may be each independently a substituted or unsubstitutedaryl group.

In another embodiment, R, R′ and R″ are the same as or different fromeach other, and may be each independently a substituted or unsubstitutedC6 to C60 aryl group.

In another embodiment, R, R′ and R″ are the same as or different fromeach other, and may be each independently a substituted or unsubstitutedC6 to C40 aryl group.

In another embodiment, R, R′ and R″ are the same as or different fromeach other, and may be each independently a C6 to C40 aryl group.

In another embodiment, R, R′ and R″ are the same as or different fromeach other, and may be each independently a phenyl group.

In the heterocyclic compound provided in one embodiment of the presentapplication, Chemical Formula 1 may be represented by any one of thefollowing Chemical Formulae 2 to 9.

In Chemical Formulae 2 to 9,

Ra, Ar₁, Ar₂, R₂ to R₅ and n have the same definitions as in ChemicalFormula 1.

In the heterocyclic compound provided in one embodiment of the presentapplication, Chemical Formula 1 is represented by any one of thefollowing compounds.

The compound according to one embodiment of the present application maybe prepared according to the following General Formula 1.

In General Formula 1, R₁₀ or R₁₁ has the same definition as Ar₁ or Ar₂of Chemical Formula 1.

In addition, by introducing various substituents to the structure ofChemical Formulae 1 to 9, compounds having unique properties of theintroduced substituents may be synthesized. For example, by introducingsubstituents normally used as hole injection layer materials, holetransfer layer materials, light emitting layer materials, electrontransfer layer materials and charge generation layer materials used formanufacturing an organic light emitting device to the core structure,materials satisfying conditions required for each organic material layermay be synthesized.

In addition, by introducing various substituents to the structure ofChemical Formulae 1 to 9, the energy band gap may be finely controlled,and meanwhile, properties at interfaces between organic materials areenhanced, and material applications may become diverse.

Meanwhile, the compound has a high glass transition temperature (Tg),and has excellent thermal stability. Such an increase in the thermalstability becomes an important factor providing driving stability to adevice.

The heterocyclic compound according to one embodiment of the presentapplication may be prepared through a multistep chemical reaction. Someintermediate compounds are prepared first, and the compound of ChemicalFormula 1 may be prepared from the intermediate compounds. Morespecifically, the heterocyclic compound according to one embodiment ofthe present application may be prepared based on preparation examples todescribe later.

Another embodiment of the present application provides an organic lightemitting device comprising a first electrode; a second electrodeprovided opposite to the first electrode; and one or more organicmaterial layers provided between the first electrode and the secondelectrode, wherein one or more layers of the organic material layerscomprise the heterocyclic compound according to Chemical Formula 1.

In one embodiment of the present application, the first electrode may bean anode, and the second electrode may be a cathode.

In another embodiment, the first electrode may be a cathode, and thesecond electrode may be an anode.

In one embodiment of the present application, the organic light emittingdevice may be a blue organic light emitting device, and the heterocycliccompound according to Chemical Formula 1 may be used as a material ofthe blue organic light emitting device.

In one embodiment of the present application, the organic light emittingdevice may be a green organic light emitting device, and theheterocyclic compound according to Chemical Formula 1 may be used as amaterial of the green organic light emitting device.

In one embodiment of the present application, the organic light emittingdevice may be a red organic light emitting device, and the heterocycliccompound according to Chemical Formula 1 may be used as a material ofthe red organic light emitting device.

Specific descriptions on the heterocyclic compound represented byChemical Formula 1 are the same as the descriptions provided above.

The organic light emitting device of the present disclosure may bemanufactured using common organic light emitting device manufacturingmethods and materials except that one or more organic material layersare formed using the heterocyclic compound described above.

The heterocyclic compound may be formed into an organic material layerthrough a solution coating method as well as a vacuum deposition methodwhen manufacturing the organic light emitting device. Herein, thesolution coating method means spin coating, dip coating, inkjetprinting, screen printing, a spray method, roll coating and the like,but is not limited thereto.

The organic material layer of the organic light emitting device of thepresent disclosure may be formed in a single layer structure, or mayalso be formed in a multilayer structure in which two or more organicmaterial layers are laminated. For example, the organic light emittingdevice according to one embodiment of the present disclosure may have astructure comprising a hole injection layer, a hole transfer layer, alight emitting layer, an electron transfer layer, an electron injectionlayer and the like as the organic material layer. However, the structureof the organic light emitting device is not limited thereto, and maycomprise less numbers of organic material layers.

In the organic light emitting device of the present disclosure, theorganic material layer comprises an electron injection layer or anelectron transfer layer, and the electron injection layer or theelectron transfer layer may comprise the heterocyclic compound.

In the organic light emitting device of the present disclosure, theorganic material layer comprises an electron transfer layer, and theelectron transfer layer may comprise the heterocyclic compound.

In another organic light emitting device, the organic material layercomprises an electron blocking layer or a hole blocking layer, and theelectron blocking layer or the hole blocking layer may comprise theheterocyclic compound.

In another organic light emitting device, the organic material layercomprises a hole blocking layer, and the hole blocking layer maycomprise the heterocyclic compound.

In another organic light emitting device, the organic material layercomprises an electron transfer layer, a light emitting layer or a holeblocking layer, and the electron transfer layer, the light emittinglayer or the hole blocking layer may comprise the heterocyclic compound.

The organic light emitting device of the present disclosure may furthercomprise one, two or more layers selected from the group consisting of alight emitting layer, a hole injection layer, a hole transfer layer, anelectron injection layer, an electron transfer layer, an electronblocking layer and a hole blocking layer.

FIGS. 1 to 3 illustrate a lamination order of electrodes and organicmaterial layers of an organic light emitting device according to oneembodiment of the present application. However, the scope of the presentapplication is not limited to these diagrams, and structures of organiclight emitting devices known in the art may also be used in the presentapplication.

FIG. 1 illustrates an organic light emitting device in which an anode(200), an organic material layer (300) and a cathode (400) areconsecutively laminated on a substrate (100). However, the structure isnot limited to such a structure, and as illustrated in FIG. 2 , anorganic light emitting device in which a cathode, an organic materiallayer and an anode are consecutively laminated on a substrate may alsobe obtained.

FIG. 3 illustrates a case of the organic material layer being amultilayer. The organic light emitting device according to FIG. 3comprises a hole injection layer (301), a hole transfer layer (302), alight emitting layer (303), a hole blocking layer (304), an electrontransfer layer (305) and an electron injection layer (306). However, thescope of the present application is not limited to such a laminationstructure, and as necessary, other layers except the light emittinglayer may not be included, and other necessary functional layers may befurther included.

The organic material layer comprising Chemical Formulae 1 to 9 mayfurther comprise other materials as necessary.

In addition, the organic light emitting device according to oneembodiment of the present application comprises an anode, a cathode, andtwo or more stacks provided between the anode and the cathode, whereinthe two or more stacks each independently comprise a light emittinglayer, a charge generation layer is included between the two or morestacks, and the charge generation layer comprises the heterocycliccompound represented by Chemical Formula 1.

In addition, the organic light emitting device according to oneembodiment of the present application may comprise an anode, a firststack provided on the anode and comprising a first light emitting layer,a charge generation layer provided on the first stack, a second stackprovided on the charge generation layer and comprising a second lightemitting layer, and a cathode provided on the second stack. Herein, thecharge generation layer may comprise the heterocyclic compoundrepresented by Chemical Formula 1. In addition, the first stack and thesecond stack may each independently further comprise one or more typesof the hole injection layer, the hole transfer layer, the hole blockinglayer, the electron transfer layer, the electron injection layerdescribed above and the like.

The charge generation layer may be an N-type charge generation layer,and the charge generation layer may further comprise a dopant known inthe art in addition to the heterocyclic compound represented by ChemicalFormula 1.

As the organic light emitting device according to one embodiment of thepresent application, an organic light emitting device having a 2-stacktandem structure is schematically illustrated in FIG. 4 .

Herein, the first electron blocking layer, the first hole blocking layerand the second hole blocking layer and the like described in FIG. 4 maynot be included in some cases.

In the organic light emitting device according to one embodiment of thepresent application, materials other than the compounds of ChemicalFormulae 1 to 9 are illustrated below, however, these are forillustrative purposes only and not for limiting the scope of the presentapplication, and may be replaced by materials known in the art.

As the anode material, materials having relatively large work functionmay be used, and transparent conductive oxides, metals, conductivepolymers or the like may be used. Specific examples of the anodematerial comprise metals such as vanadium, chromium, copper, zinc andgold, or alloys thereof; metal oxides such as zinc oxide, indium oxide,indium tin oxide (ITO) and indium zinc oxide (IZO); combinations ofmetals and oxides such as ZnO:Al or SnO₂:Sb; conductive polymers such aspoly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole and polyaniline, and the like, but are not limitedthereto.

As the cathode material, materials having relatively small work functionmay be used, and metals, metal oxides, conductive polymers or the likemay be used. Specific examples of the cathode material comprise metalssuch as magnesium, calcium, sodium, potassium, titanium, indium,yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloysthereof; multilayer structure materials such as LiF/Al or LiO₂/Al, andthe like, but are not limited thereto.

As the hole injection material, known hole injection materials may beused, and for example, phthalocyanine compounds such as copperphthalocyanine disclosed in U.S. Pat. No. 4,356,429, or starburst-typeamine derivatives such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA),4,4′,4″-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA) or1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB)described in the literature [Advanced Material, 6, p. 677 (1994)],polyaniline/dodecylbenzene sulfonic acid,poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate),polyaniline/camphor sulfonic acid orpolyaniline/poly(4-styrene-sulfonate) that are conductive polymershaving solubility, and the like, may be used.

As the hole transfer material, pyrazoline derivatives, arylamine-basedderivatives, stilbene derivatives, triphenyldiamine derivatives and thelike may be used, and low molecular or high molecular materials may alsobe used.

As the electron transfer material, metal complexes of oxadiazolederivatives, anthraquinodimethane and derivatives thereof, benzoquinoneand derivatives thereof, naphthoquinone and derivatives thereof,anthraquinone and derivatives thereof, tetracyanoanthraquinodimethaneand derivatives thereof, fluorenone derivatives, diphenyldicyanoethyleneand derivatives thereof, diphenoquinone derivatives, 8-hydroxyquinolineand derivatives thereof, and the like, may be used, and high molecularmaterials may also be used as well as low molecular materials.

As examples of the electron injection material, LiF is typically used inthe art, however, the present application is not limited thereto.

As the light emitting material, red, green or blue light emittingmaterials may be used, and as necessary, two or more light emittingmaterials may be mixed and used. Herein, two or more light emittingmaterials may be used by being deposited as individual sources of supplyor by being premixed and deposited as one source of supply. In addition,fluorescent materials may also be used as the light emitting material,however, phosphorescent materials may also be used. As the lightemitting material, materials emitting light by bonding electrons andholes injected from an anode and a cathode, respectively, may be usedalone, however, materials having a host material and a dopant materialinvolved in light emission together may also be used.

When mixing light emitting material hosts, same series hosts may bemixed, or different series hosts may be mixed. For example, any two ormore types of materials among n-type host materials or p-type hostmaterials may be selected, and used as a host material of a lightemitting layer.

The organic light emitting device according to one embodiment of thepresent application may be a top-emission type, a bottom-emission typeor a dual-emission type depending on the materials used.

The heterocyclic compound according to one embodiment of the presentapplication may also be used in an organic electronic device comprisingan organic solar cell, an organic photo conductor, an organic transistorand the like under a similar principle used in the organic lightemitting device.

Hereinafter, the present specification will be described in more detailwith reference to examples, however, these are for illustrative purposesonly, and the scope of the present application is not limited thereto.

PREPARATION EXAMPLE <Preparation Example 1> Preparation of Compound 1

1) Preparation of Compound 1-1

After dissolving (1H-indol-2-yl)boronic acid (100 g, 0.621 mol) and2-bromoaniline (96 g, 0.558 mol) in toluene, EtOH and H₂O (1000 mL:200mL:200 mL), Pd(PPh₃)₄ (35.8 g, 0.031 mol) and NaHCO₃ (156.5 g, 1.863mol) were introduced thereto, and the result was stirred for 3 hours at100° C. After the reaction was completed, MC(Methylene Chloride) anddistilled water were introduced to the reaction solution for extraction.After that, the result was dried with anhydrous MgSO₄, and the solventwas removed using a rotary evaporator to obtain Compound 1-1 (94 g, 72%)in a liquid form.

2) Preparation of Compound 1-2

Compound 1-1 (94 g, 0.451 mol) and triethylamine (42 mL, 0.451 mol) wereintroduced to MC (1200 mL) and dissolved therein. 4-Bromobenzoylchloride (108.9 g, 0.496 mol) dissolved in MC (300 mL) was slowly addeddropwise to the mixture at 0° C. After the reaction was completed, MCand distilled water were introduced to the reaction solution forextraction. After that, the result was dried with anhydrous MgSO₄, andthe solvent was removed using a rotary evaporator to obtain Compound 1-2(150 g, 85%) in a liquid form.

3) Preparation of Compound 1-3

After dissolving Compound 1-2 (150 g, 0.383 mol) in nitrobenzene (1500mL), POCl₃ (35 mL, 0.383 mol) was slowly added dropwise thereto. Theresult was reacted for 15 hours at 140° C. After the reaction wascompleted, a solution dissolving NaHCO₃ in distilled water was slowlyintroduced to the reaction solution, and the result was stirred.Produced solids were filtered and collected. The collected solids wererecrystallized with MC and MeOH to obtain Compound 1-3 (68 g, 48%) in asolid form.

4) Preparation of Compound 1-4

After dissolving Compound 1-3 (10 g, 0.026 mol), bis(pinacolato)diboron(9.9 g, 0.039 mol), KOAc (7.6 g, 0.078 mol) and PdCl₂(dppf) (0.9 g,0.0013 mol) in 1,4-dioxane (200 mL), the result was reacted for 5 hoursat 90° C. After the reaction was completed, MC and distilled water wereintroduced to the reaction solution for extraction. After that, theresult was dried with anhydrous MgSO₄, and the solvent was removed usinga rotary evaporator to obtain Compound 1-4 (10 g, 91%).

5) Preparation of Compound 1-5

After dissolving Compound 1-4 (10 g, 0.023 mol) and2-bromo-4,6-diphenyl-1,3,5-triazine (7 g, 0.023 mol) in toluene, EtOHand H₂O (100 mL:20 mL:20 mL), Pd(PPh₃)₄ (1.3 g, 0.0011 mol) and K₂CO₃(9.5 g, 0.069 mol) were introduced thereto, and the result was stirredfor 5 hours at 100° C. After the reaction was completed, MC anddistilled water were introduced to the reaction solution for extraction.After that, the result was dried with anhydrous MgSO₄, and the solventwas removed using a rotary evaporator to obtain Compound 1-5 (9 g, 74%).

6) Preparation of Compound 1

After dissolving Compound 1-5 (9 g, 0.017 mol) and bromobenzene (3.2 g,0.021 mol) in toluene (100 mL), Pd₂(dba)₃ (1.5 g, 0.0017 mol),tri-tert-butylphosphine (0.6 g, 0.034 mol) and sodium tert-butoxide (4.9g, 0.051 mol) were introduced thereto, and the result was stirred for 15hours at 100° C. After the reaction was completed, the result was cooledto room temperature, and produced solids were filtered and dried toobtain Compound 1 (7.5 g, 73%).

A target compound was synthesized in the same manner as in PreparationExample 1 except that Intermediate A of the following Table 1 was usedinstead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

TABLE 1 Com- pound Num- ber Intermediate A Target Compound Yield 2

61% 4

65% 6

66% 7

64% 8

69% 26

71% 28

77% 31

70% 33

54% 66

61% 68

66% 70

64% 73

65% 74

66% 77

68% 78

66% 88

66% 93

64% 96

60% 100

61% 101

60% 104

64% 105

61% 108

59% 117

58% 131

65% 132

61%

A target compound was synthesized in the same manner as in PreparationExample 1 except that Intermediate B of the following Table 2 was usedinstead of 4-bromobenzoyl chloride, and Intermediate C of the followingTable 2 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

TABLE 2 Com- pound Num- Intermediate ber B Intermediate C Compound Yield16

60% 21

64% 35

66% 37

61% 39

63% 41

63% 42

64% 115

66% 120

62%

A target compound was synthesized in the same manner as in PreparationExample 1 except that Intermediate D of the following Table 3 was usedinstead of 2-bromoaniline, and Intermediate E of the following Table 3was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

TABLE 3 Com- pound Num- Intermediate Intermediate ber D E Compound Yield45

51% 59

52% 65

49%

<Preparation Example 2> Preparation of Compound 135

1) Preparation of Compound 135-1

After dissolving (1H-indol-2-yl)boronic acid (100 g, 0.621 mol) and2-bromoaniline (96 g, 0.558 mol) in toluene, EtOH and H₂O (1000 mL:200mL:200 mL), Pd(PPh₃)₄ (35.8 g, 0.031 mol) and NaHCO₃ (156.5 g, 1.863mol) were introduced thereto, and the result was stirred for 3 hours at100° C. After the reaction was completed, MC and distilled water wereintroduced to the reaction solution for extraction. After that, theresult was dried with anhydrous MgSO₄, and the solvent was removed usinga rotary evaporator to obtain Compound 135-1 (94 g, 72%) in a liquidform.

2) Preparation of Compound 135-2

Compound 135-1 (94 g, 0.451 mol) and triethylamine (42 mL, 0.451 mol)were introduced to MC (1200 mL) and dissolved therein. Benzoyl chloride(69.7 g, 0.496 mol) dissolved in MC (300 mL) was slowly added dropwiseto the mixture at 0° C. After the reaction was completed, MC anddistilled water were introduced to the reaction solution for extraction.After that, the result was dried with anhydrous MgSO₄, and the solventwas removed using a rotary evaporator to obtain Compound 135-2 (112 g,80%) in a liquid form.

3) Preparation of Compound 135-3

After dissolving Compound 135-2 (112 g, 0.358 mol) in nitrobenzene (1000mL), POCl₃ (33 mL, 0.358 mol) was slowly added dropwise thereto. Theresult was reacted for 15 hours at 140° C. After the reaction wascompleted, a solution dissolving NaHCO₃ in distilled water was slowlyintroduced to the reaction solution, and the result was stirred.Produced solids were filtered and collected. The collected solids wererecrystallized with MC and MeOH to obtain Compound 135-3 (54 g, 51%) ina solid form.

4) Preparation of Compound 135

After dissolving Compound 135-3 (9 g, 0.030 mol) and4-(4-bromophenyl)-2,6-diphenylpyrimidine (11.8 g, 0.030 mol) in toluene(100 mL), Pd₂(dba)₃ (2.8 g, 0.003 mol), tri-tert-butylphosphine (1.2 g,0.006 mol) and sodium tert-butoxide (5.7 g, 0.062 mol) were introducedthereto, and the result was stirred for 15 hours at 100° C. After thereaction was completed, the result was cooled to room temperature, andproduced solids were filtered and dried to obtain Compound 135 (9.4 g,52%).

A target compound was synthesized in the same manner as in PreparationExample 2 except that Intermediate F of the following Table 4 was usedinstead of 4-(4-bromophenyl)-2,6-diphenylpyrimidine.

TABLE 4 Com- pound Num- ber Intermediate F Compound Yield 134

56% 137

55% 139

59% 141

61% 143

66% 148

63% 149

58% 152

59% 155

65% 156

63% 157

66% 158

63% 159

63% 161

66% 165

66% 168

60% 169

61% 203

65% 205

61% 209

60% 212

61% 234

61% 236

58%

A target compound was synthesized in the same manner as in PreparationExample 2 except that Intermediate G of the following Table 5 was usedinstead of benzoyl chloride, and Intermediate H of the following Table 5was used instead of 4-(4-bromophenyl)-2,6-diphenylpyrimidine.

TABLE 5 Com- pound Num- Intermediate ber G Intermediate H Compound Yield213

45% 218

51% 219

54% 222

51% 228

53% 229

53%

A target compound was synthesized in the same manner as in PreparationExample 2 except that Intermediate I of the following Table 6 was usedinstead of 2-bromoaniline, and Intermediate J of the following Table 6was used instead of 4-(4-bromophenyl)-2,6-diphenylpyrimidine.

TABLE 6 Com- pound Num- ber Intermediate I Intermediate J Compound Yield187

49% 192

50% 195

51%

<Preparation Example 3> Preparation of Compound 237

1) Preparation of Compound 237-1

After dissolving (1H-indol-3-yl)boronic acid (100 g, 0.621 mol) and2-bromoaniline (96 g, 0.558 mol) in toluene, EtOH and H₂O (1000 mL:200mL:200 mL), Pd(PPh₃)₄ (35.8 g, 0.031 mol) and NaHCO₃ (156.5 g, 1.863mol) were introduced thereto, and the result was stirred for 3 hours at100° C. After the reaction was completed, MC and distilled water wereintroduced to the reaction solution for extraction. After that, theresult was dried with anhydrous MgSO₄, and the solvent was removed usinga rotary evaporator to obtain Compound 237-1 (94 g, 72%) in a liquidform.

2) Preparation of Compound 237-2

Compound 237-1 (94 g, 0.451 mol) and triethylamine (42 mL, 0.451 mol)were introduced to MC (1200 mL) and dissolved therein. 4-Bromobenzoylchloride (108.9 g, 0.496 mol) dissolved in MC (300 mL) was slowly addeddropwise to the mixture at 0° C. After the reaction was completed, MCand distilled water were introduced to the reaction solution forextraction. After that, the result was dried with anhydrous MgSO₄, andthe solvent was removed using a rotary evaporator to obtain Compound237-2 (150 g, 85%) in a liquid form.

3) Preparation of Compound 237-3

After dissolving Compound 237-2 (150 g, 0.383 mol) in nitrobenzene (1500mL), POCl₃ (35 mL, 0.383 mol) was slowly added dropwise thereto. Theresult was reacted for 15 hours at 140° C. After the reaction wascompleted, a solution dissolving NaHCO₃ in distilled water was slowlyintroduced to the reaction solution, and the result was stirred.Produced solids were filtered and collected. The collected solids wererecrystallized with MC and MeOH to obtain Compound 237-3 (68 g, 48%) ina solid form.

4) Preparation of Compound 237-4

After dissolving Compound 237-3 (10 g, 0.026 mol),bis(pinacolato)diboron (9.9 g, 0.039 mol), KOAc (7.6 g, 0.078 mol) andPdCl₂(dppf) (0.9 g, 0.0013 mol) in 1,4-dioxane (200 mL), the result wasreacted for 5 hours at 90° C. After the reaction was completed, MC anddistilled water were introduced to the reaction solution for extraction.After that, the result was dried with anhydrous MgSO₄, and the solventwas removed using a rotary evaporator to obtain Compound 237-4 (10 g,91%).

5) Preparation of Compound 237-5

After dissolving Compound 237-4 (8 g, 0.019 mol) and2-bromo-4,6-diphenyl-1,3,5-triazine (5.9 g, 0.019 mol) in toluene, EtOHand H₂O (80 mL:10 mL:10 mL), Pd(PPh₃)₄ (1.1 g, 0.0009 mol) and K₂CO₃(7.8 g, 0.057 mol) were introduced thereto, and the result was stirredfor 5 hours at 100° C. After the reaction was completed, MC anddistilled water were introduced to the reaction solution for extraction.After that, the result was dried with anhydrous MgSO₄, and the solventwas removed using a rotary evaporator to obtain Compound 237-5 (7.4 g,75%).

6) Preparation of Compound 237

After dissolving Compound 237-5 (7.4 g, 0.014 mol) and bromobenzene (3.2g, 0.021 mol) in toluene (100 mL), Pd₂(dba)₃ (1.2 g, 0.0014 mol),tri-tert-butylphosphine (0.5 g, 0.0028 mol) and sodium tert-butoxide(2.7 g, 0.028 mol) were introduced thereto, and the result was stirredfor 15 hours at 100° C. After the reaction was completed, the result wascooled to room temperature, and produced solids were filtered and driedto obtain Compound 237 (6.5 g, 77%).

A target compound was synthesized in the same manner as in PreparationExample 3 except that Intermediate K of the following Table 7 was usedinstead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

TABLE 7 Compound Number Intermediate K Compound Yield 238

70% 240

68% 242

72% 259

73% 263

75% 264

69% 277

58% 278

55% 282

59% 283

64% 284

66% 288

68% 290

65% 292

67% 293

69% 296

67% 299

64% 300

61% 303

66% 304

64% 306

62% 308

61%

A target compound was synthesized in the same manner as in PreparationExample 3 except that Intermediate L of the following Table 8 was usedinstead of 4-bromobenzoyl chloride, and Intermediate M of the followingTable 8 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

TABLE 8 Com- pound Number Intermediate L Intermediate M Compound Yield248

70% 250

74% 251

73% 253

73% 267

69% 270

70% 273

72% 305

71% 313

72%

A target compound was synthesized in the same manner as in PreparationExample 3 except that Intermediate N of the following Table 9 was usedinstead of 2-bromoaniline, and Intermediate 0 of the following Table 9was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

TABLE 9 Compound Number Intermediate N Intermediate O Compound Yield 399

50% 400

51% 401

59%

<Preparation Example 4> Preparation of Compound 345

1) Preparation of Compound 345-1

After dissolving (1H-indol-3-yl)boronic acid (100 g, 0.621 mol) and2-bromoaniline (96 g, 0.558 mol) in toluene, EtOH and H₂O (1000 mL:200mL:200 mL), Pd(PPh₃)₄ (35.8 g, 0.031 mol) and NaHCO₃ (156.5 g, 1.863mol) were introduced thereto, and the result was stirred for 3 hours at100° C. After the reaction was completed, MC and distilled water wereintroduced to the reaction solution for extraction. After that, theresult was dried with anhydrous MgSO₄, and the solvent was removed usinga rotary evaporator to obtain Compound 345-1 (94 g, 72%) in a liquidform.

2) Preparation of Compound 345-2

Compound 345-1 (94 g, 0.451 mol) and triethylamine (42 mL, 0.451 mol)were introduced to MC (1200 mL) and dissolved therein. Benzoyl chloride(69.7 g, 0.496 mol) dissolved in MC (300 mL) was slowly added dropwiseto the mixture at 0° C. After the reaction was completed, MC anddistilled water were introduced to the reaction solution for extraction.After that, the result was dried with anhydrous MgSO₄, and the solventwas removed using a rotary evaporator to obtain Compound 345-2 (112 g,80%) in a liquid form.

3) Preparation of Compound 345-3

After dissolving Compound 345-2 (112 g, 0.358 mol) in nitrobenzene (1000mL), POCl₃ (33 mL, 0.358 mol) was slowly added dropwise thereto. Theresult was reacted for 15 hours at 140° C. After the reaction wascompleted, a solution dissolving NaHCO₃ in distilled water was slowlyintroduced to the reaction solution, and the result was stirred.Produced solids were filtered and collected. The collected solids wererecrystallized with MC and MeOH to obtain Compound 345-3 (54 g, 51%) ina solid form.

4) Preparation of Compound 345

After dissolving Compound 345-3 (9 g, 0.030 mol),2,4-di([1,1′-biphenyl]-4-yl)-6-(4-bromophenyl)pyrimidine (4.7 g, 0.030mol) in toluene (100 mL), Pd₂(dba)₃ (2.8 g, 0.003 mol),tri-tert-butylphosphine (1.2 g, 0.006 mol) and sodium tert-butoxide (5.7g, 0.062 mol) were introduced thereto, and the result was stirred for 15hours at 100° C. After the reaction was completed, the result was cooledto room temperature, and produced solids were filtered and dried toobtain Compound 345 (15 g, 60%).

A target compound was synthesized in the same manner as in PreparationExample 4 except that Intermediate P of the following Table 10 was usedinstead of 2,4-di([1,1′-biphenyl]-4-yl)-6-(4-bromophenyl)pyrimidine.

TABLE 10 Compound Number Intermediate P Compound Yield 321

69% 324

68% 325

66% 332

66% 336

66% 339

68% 343

67% 352

68% 353

67% 370

61% 372

60% 373

64% 374

63% 376

61% 379

66% 380

61% 381

64% 382

61% 384

59% 397

59% 396

60% 398

61%

A target compound was synthesized in the same manner as in PreparationExample 4 except that Intermediate Q of the following Table 11 was usedinstead of benzoyl chloride, and Intermediate R of the following Table11 was used instead of2,4-di([1,1′-biphenyl]-4-yl)-6-(4-bromophenyl)pyrimidine.

TABLE 11 Com- pound Number Intermediate Q Intermediate R Compound Yield388

60% 391

55% 395

51%

A target compound was synthesized in the same manner as in PreparationExample 4 except that Intermediate S of the following Table 12 was usedinstead of 2-bromoaniline, and Intermediate T of the following Table 12was used instead of2,4-di([1,1′-biphenyl]-4-yl)-6-(4-bromophenyl)pyrimidine.

TABLE 12 Com- pound Number Intermediate S Intermediate T Compound Yield363

50% 365

51% 367

52%

Compounds other than the compounds described in Table 1 to Table 12 werealso prepared in the same manner as in the preparation examplesdescribed above.

The following Table 13 and Table 14 present 1H NMR data and FD-MS dataof the synthesized compounds, and through the following data, synthesesof target compounds may be identified.

TABLE 13 NO ¹H NMR (CDCl₃, 300 Mz) 1 δ = 8.69(2H, d), 8.55(1H, d),8.42(1H, d), 8.36(4H, d), 7.96~7.85(6H, m), 7.62~7.50(11H, m), 7.35(1H,t), 7.16(1H, t) 2 δ = 8.69(2H, d), 8.55(1H, d), 8.42~8.30(5H, m),7.94~7.87(6H, m), 7.62~7.50(11H, m), 7.35(1H, t), 7.16(1H, t) 4 δ =8.69(2H, d), 8.55(1H, d), 8.42~8.36(3H, m), 7.96~7.85(8H, m), 7.75(2H,d), 7.62~7.35(12H, m), 7.25(2H, d), 7.16(1H, t) 6 δ = 8.69(2H, d),8.55(1H, d), 8.42(1H, d), 8.30(2H, d), 8.23(1H, s), 7.94~7.85(10H, m),7.75(1H, d), 7.62~7.49(12H, m), 7.16(1H, t) 7 δ = 8.69(2H, d), 8.55(1H,d), 8.42(1H, d), 7.96(10H, m), 7.75(4H, d), 7.62~7.41(12H, m), 7.25(4H,m), 7.16(1H, t) 8 δ = 8.69(2H, d), 8.55(1H, d), 8.42(d, 1H), 8.30(4H,d), 8.23(1H, s), 7.94~7.75(14H, m), 7.62~7.41(12H, m), 7.16(1H, t) 16 δ= 8.97(2H, d), 8.68(1H, d), 8.55(1H, d), 8.42(1H, d), 8.29(1H, d),8.23(1H, s), 7.94~7.85(7H, m), 7.62~7.49(13H, m), 7.35(1H, t), 7.16(1H,t) 21 δ = 8.97(2H, d), 8.68(1H, d), 8.55(1H, d), 8.42(1H, d), 8.30(4H,d), 8.29(1H, d), 8.23(1H, s), 7.94~7.75(12H, m), 7.62~7.41(14H, m),7.16(1H, t) 26 δ = 8.69(2H, d), 8.55(1H, d), 8.42(1H, d), 8.23(1H, s),7.94~7.85(12H, m), 7.62~7.49(11H, m), 7.35(1H, t), 7.25(2H, d), 7.16(1H,t) 28 δ = 8.69(2H, d), 8.55(1H, d), 8.42(1H, d), 8.35~8.30(6H, m),7.94~7.85(10H, m), 7.75(2H, d), 7.62~7.35(12H, m), 7.16(1H, t) 31 δ =8.69(2H, d), 8.55(1H, d), 8.42(1H, d), 8.30(4H, d), 8.23(1H, s),7.96~7.85(12H, m), 7.75(4H, d), 7.62~7.41(12H, m), 7.25(2H, d), 7.16(1H,t) 33 δ = 9.18(2H, d), 8.14(2H, d), 8.69(2H, d), 8.55(2H, d), 8.42(1H,d), 7.94(2H, d), 7.85(4H, d), 7.74(2H, t), 7.62~7.50(5H, m), 7.35(1H,t), 7.25~7.16(7H, m) 35 δ = 8.55(1H, d), 8.42~8.33(8H, m), 7.94~7.85(4H,m), 7.73(1H, t), 7.62~7.50(11H, m), 7.35(1H, t), 7.16(1H, t) 37 δ =8.55(1H, d), 8.42~8.33(4H, m), 8.23(1H, s), 7.94~7.85(8H, m), 7.73(1H,t), 7.62~7.49(11H, m), 7.35(1H, t), 7.16(1H, t) 39 δ = 8.55(1H, d),8.42~8.30(7H, m), 8.23(1H, s), 7.94~7.85(7H, m), 7.75(2H, d), 7.73(1H,t), 7.62~7.35(12H, m), 7.16(1H, t) 41 δ = 8.55(1H, d), 8.42~8.33(4H, m),7.96~7.85(8H, m), 7.75~7.73(5H, m), 7.62~7.35(12H, m), 7.25(4H, d),7.16(1H, t) 42 δ = 8.55(1H, d), 8.42~8.30(8H, m), 8.23(1H, s),7.94~7.75(13H, m), 7.62~7.35(12H, m), 7.16(1H, t) 45 δ = 8.69(2H, d),8.51(2H, d), 8.36(4H, d), 8.20(1H, d), 8.11(1H, d), 7.96(2H, d),7.94(1H, d), 7.90(1H, d), 7.72~7.50(13H, m), 7.35(1H, t), 7.16(1H, t) 59δ = 8.69(2H, d), 8.55(1H, d), 8.28(1H, d), 8.11(1H, d), 8.03(1H, s),7.96~7.94(7H, m), 7.79~7.41(23H, m), 7.16(1H, t) 65 δ = 8.69(2H, d),8.55(2H, d), 8.35(2H, d), 8.30(2H, d), 8.23(1H, s), 8.09~7.85(10H, m),7.62~7.49(13H, m), 7.35(1H, t), 7.25(2H, d), 7.16(1H, t) 66 δ = 8.79(1H,d), 8.69(2H, d), 8.55(1H, d), 8.42~8.30(6H, m), 8.15(1H, d),7.96~7.85(6H, m), 7.70~7.50(13H, m), 7.35(1H, t), 7.16(1H, t) 68 δ =8.79(1H, d), 8.69(2H, d), 8.55(1H, d), 8.42(1H, d), 8.33(2H, d),8.30(1H, d), 8.23(1H, s), 8.15(1H, d), 7.96~7.85(8H, m), 7.70~7.49(13H,m), 7.35(1H, t), 7.16(1H, t) 70 δ = 8.69(2H, d), 8.55(1H, d), 8.42(1H,d), 8.38(2H, d), 7.94~7.85(8H, m), 7.75~7.73(4H, m), 7.61~7.35(14H, m),7.16(1H, t) 73 δ = 8.69(2H, d), 8.55(1H, d), 8.42(1H, d), 8.23(1H, s),7.96~7.85(10H, m), 7.75(2H, d), 7.73(1H, t), 7.62~7.35(13H, m), 7.16(1H,t) 74 δ = 8.69(2H, d), 8.55(1H, d), 8.42(1H, d), 8.38(1H, t), 8.30(2H,d), 8.23(1H, s), 7.94~7.87(7H, m), 7.75(2H, d), 7.73(1H, t),7.62~7.41(13H, m), 7.16(1H, t) 77 δ = 8.69(2H, d), 8.55(2H, d), 8.42(1H,d), 8.36(2H, d), 8.19(1H, d), 7.96~7.85(7H, m), 7.62~7.50(10H, m),7.35(2H, t), 7.20(1H, t), 7.16(2H, t) 78 δ = 8.69(2H, d), 8.55(1H, d),8.42(1H, d), 8.36(2H, d), 8.19(1H, d), 7.94~7.85(11H, m), 7.62~7.50(10H,m), 7.35(1H, t), 7.20~7.16(3H, t) 88 δ = 8.69(2H, d), 8.55(1H, d),8.42(1H, d), 8.36(2H, d), 8.09(1H, d), 7.94~7.78(9H, m), 7.62~7.50(9H,m), 7.38(1H, t), 7.35(1H, t), 7.28(1H, t), 1.69(6H, s) 93 δ = 8.69(2H,d), 8.55(1H, d), 8.42(1H, d), 8.35(2H, d), 8.30(2H, d), 8.23(1H, s),8.09(1H, d), 7.94~7.73(10H, m), 7.62~7.50(10H, m), 7.38~7.28(3H, m),7.16(1H, t), 1.69(6H, s) 96 δ = 8.69(2H, d), 8.55(1H, d), 8.42(1H, d),8.36(2H, d), 7.96~7.82(10H, m), 7.62~7.50(8H, m), 7.35(1H, t), 7.16(1H,t) 100 δ = 8.69(2H, d), 8.55(1H, d), 8.42(1H, d), 7.96~7.75(14H, m),7.62~7.35(9H, m), 7.25(2H, d), 7.16(1H, t) 101 δ = 8.69(2H, d), 8.55(1H,d), 8.42(1H, d), 7.94~7.75(14H, m), 7.62~7.35(10H, m), 7.16(1H, t) 104 δ= 9.08(1H, d), 8.84(1H, d), 8.69(2H, d), 8.55(1H, d), 8.42(1H, d),8.36(2H, d), 8.27(1H, d), 8.05(1H, s), 7.96~7.85(9H, m), 7.70~7.50(12H,m), 7.35(1H, t), 7.25(2H, d), 7.16(1H, t) 105 δ = 9.27(1H, d), 8.85(1H,d), 8.69(2H, d), 8.55(1H, d), 8.42(1H, d), 8.36(2H, d), 8.15(1H, d),7.96~7.85(7H, m), 7.75~7.50(12H, m), 7.35(1H, t), 7.16(1H, t) 108 δ =8.69(2H, d), 8.55(1H, d), 8.42(1H, d), 8.36(2H, d), 8.04(3H, s),7.96~7.85(6H, m), 7.75(4H, d), 7.62~7.35(15H, m), 7.16(1H, t) 115 δ =8.95(1H, d), 8.55(1H, d), 8.45~8.42(2H, d), 8.30~8.20(5H, m),7.94~7.85(10H, m), 7.62~7.35(14H, m), 7.25(2H, d), 7.16(1H, t) 117 δ =8.93(1H, d), 8.69(2H, d), 8.55(1H, d), 8.42~8.23(8H, m), 7.94~7.85(6H,m), 7.72(1H, d), 7.62~7.35(14H, m), 7.25(4H, m), 7.16(1H, t) 120 δ =8.95(1H, d), 8.55(1H, d), 8.45(1H, d), 8.42(1H, d), 8.25(1H, d),8.23(1H, s), 8.20(1H, d), 7.94~7.85(10H, m), 7.75(4H, d), 7.73(2H, d),7.62~7.35(16H, m), 7.25(2H, d), 7.16(1H, t) 131 δ = 9.02(1H, d),8.95(1H, d), 8.69(2H, d), 8.55(1H, d), 8.42(1H, d), 8.36(4H, d),8.06(1H, d), 7.94~7.84(5H, m), 7.62~7.46(13H, m), 7.35(1H, t), 7.25(2H,d), 7.16(1H, t) 132 δ = 9.02(1H, d), 8.95(1H, d), 8.69(2H, d), 8.55(1H,d), 8.42(1H, d), 8.35(2H, d), 8.23(1H, s), 8.06(1H, d), 7.94~7.84(7H,m), 7.62~7.49(13H, m), 7.35(1H, t), 7.25(2H, d), 7.16(1H, t) 134 δ =8.55(1H, d), 8.42~8.36(5H, m), 8.19(2H, d), 7.94~7.85(8H, m), 7.65(2H,d), 7.50~7.49(7H, m), 7.35(1H, t), 7.16(1H, t) 135 δ = 8.55(1H, d),8.42(1H, d), 8.35(2H, d), 8.23(1H, s), 8.19(2H, d), 7.94~7.87(10H, m),7.65(2H, t), 7.55~7.49(7H, m), 7.35(1H, t), 7.16(1H, t) 137 δ = 8.55(1H,d), 8.42~8.36(3H, d), 8.19(2H, d), 7.96~7.85(10H, m), 7.75(2H, d),7.65(2H, t), 7.50~7.35(8H, m), 7.25(2H, d), 7.16(1H, t) 139 δ = 8.55(1H,d), 8.42(1H, d), 8.30(2H, d), 8.23(1H, s), 8.19(2H, d), 7.94~7.85(12H,m), 7.75(2H, d), 7.65(2H, t), 7.55~7.35(8H, m), 7.16(1H, t) 141 δ =8.55(1H, d), 8.42(1H, d), 8.30~8.19(7H, m), 7.94~7.75(16H, m), 7.65(2H,t), 7.49~7.35(8H, m), 7.16(1H, t) 143 δ = 8.97(1H, d), 8.55(1H, d),8.42~8.36(5H, m), 8.24~8.12(4H, m), 7.94~7.79(5H, m), 7.65~7.49(11H, m),7.35(1H, t), 7.16(1H, t) 148 δ = 8.97(1H, d), 8.55(1H, d), 8.42(1H, d),8.30~8.12(7H, m), 7.94~7.35(23H, m), 7.16(1H, t) 149 δ = 8.97(1H, d),8.55(1H, d), 8.42(1H, d), 8.24~8.19(3H, d), 7.94~7.35(25H, m), 7.25(4H,d), 7.16(1H, t) 152 δ = 8.80(1H, d), 8.71(1H, d), 8.55(1H, d), 8.45(1H,d), 8.42(1H, d), 8.30(2H, d), 8.20(1H, d), 8.19(2H, d), 7.94~7.85(7H,m), 7.65~7.49(4H, m), 7.35(1H, t), 7.29(1H, d), 7.16(1H, t) 155 δ =8.55(1H, d), 8.42(1H, d), 8.23(1H, s), 8.19(2H, d), 7.94~7.85(14H, m),7.65(2H, t), 7.55~7.49(7H, m), 7.35(1H, t), 7.25(2H, d), 7.16(1H, t) 156δ = 8.71(2H, d), 8.55(1H, d), 8.42(1H, d), 8.33(2H, d), 8.30(2H, d),8.20(1H, d), 8.19(2H, d), 7.94~7.85(7H, m), 7.65~7.49(6H, m), 7.35(1H,t), 7.29(2H, d), 7.16(1H, t) 157 δ = 8.71(2H, d), 8.69(2H, d), 8.55(1H,d), 8.42(1H, d), 8.33(2H, d), 8.19(2H, d), 7.94~7.85(11H, m),7.65~7.49(6H, m), 7.35(1H, t), 7.29(2H, d), 7.16(1H, t) 158 δ = 8.71(2H,d), 8.55(1H, d), 8.42(1H, d), 8.33(4H, d), 8.19(2H, d), 7.94~7.85(9H,m), 7.73~7.49(8H, m), 7.35~7.29(3H, m), 7.16(1H, t) 159 δ = 8.55(1H, d),8.42(1H, d), 8.19(2H, d), 7.96~7.85(14H, m), 7.75(4H, d), 7.65(2H, t),7.49~7.35(8H, m), 7.25~7.16(7H, m), 161 δ = 9.18(2H, d), 9.14(2H, s),8.55(3H, d), 8.42(1H, d), 8.19(2H, d), 7.94~7.85(8H, m), 7.74~7.65(4H,d), 7.49(1H, t), 7.35(1H, t), 7.25~7.16(7H, m) 165 δ = 8.55(1H, d),8.42~8.36(5H, m), 8.24(2H, d), 8.19(2H, d), 7.94~7.85(4H, m),7.68~7.60(4H, m), 7.50(7H, t), 7.35(1H, t), 7.16(1H, t) 168 δ = 8.55(1H,d), 8.42~8.36(3H, d), 8.24~8.19(4H, d), 7.96~7.85(6H, m), 7.75~7.60(6H,m), 7.50~7.35(8H, m), 7.25(2H, d), 7.16(1H, t) 169 δ = 8.55(1H, d),8.42~8.30(5H, m), 8.23~8.19(4H, m), 7.94~7.65(13H, m), 7.50~7.35(8H, m),7.16(1H, t) 187 δ = 8.55(2H, d), 8.51(1H, d), 8.36(2H, d), 8.24~8.11(6H,m), 7.99~7.90(9H, m), 7.77~7.60(9H, m), 7.50~7.35(9H, m), 7.16(1H, t)192 δ = 8.55(1H, d), 8.35~7.91(18H, m), 7.75~7.65(5H, m), 7.50~7.25(11H,m), 7.16(1H, t) 195 δ = 8.55(2H, d), 8.35(2H, d), 8.23(1H, s), 8.19(2H,d), 8.06~7.91(10H, m), 7.65~7.49(11H, m), 7.35(1H, t), 7.16(1H, t) 203 δ= 8.55(1H, d), 8.42~8.36(3H, d), 8.19(2H, d), 7.98~7.79(12H, m),7.65(2H, t), 7.54~7.49(5H, m), 7.39(1H, t), 7.35(1H, t), 7.31(1H, t),7.16(1H, t) 205 δ = 8.55(1H, d), 8.42(1H, d), 8.35(2H, d), 8.30(2H, d),8.23(1H, s), 8.19(2H, d), 7.98~7.82(10H, m), 7.69~7.49(9H, m),7.39~7.25(5H, m), 7.16(1H, t) 209 δ = 8.55(2H, d), 8.45~8.36(4H, d),8.19(2H, d), 7.94~7.85(10H, m), 7.70~7.49(9H, m), 7.35(1H, t), 7.16(1H,t) 212 δ = 8.55(2H, d), 8.45~8.32(5H, m), 8.23(1H, s), 8.19(2H, d),7.94~7.85(11H, m), 7.73~7.49(11H, m), 7.35(1H, t), 7.16(1H, t) 213 δ =8.55(1H, d), 8.42(2H, d), 8.36(4H, d), 8.21(1H, d), 8.10(2H, t),7.94~7.80(10H, m), 7.69(1H, d), 7.55~7.50(7H, m), 7.35(1H, t), 7.16(1H,t) 218 δ = 9.08(1H, d), 8.84(1H, d), 8.55(1H, d), 8.44(1H, s),8.42~8.36(3H, d), 8.17(1H, d), 7.96~7.85(11H, m), 7.75~7.62(6H, m),7.50~7.35(7H, m), 7.25(2H, d), 7.16(1H, s) 219 δ = 9.08(1H, d), 8.84(1H,d), 8.55(1H, d), 8.44~8.30(6H, m), 8.23(1H, s), 8.17(1H, d),7.94~7.85(11H, m), 7.75~7.62(6H, m), 7.50~7.35(7H, m), 7.16(1H, d) 222 δ= 9.08(1H, d), 8.84(1H, d), 8.55(1H, d), 8.44~8.42(2H, d), 8.30(4H, d),8.23(1H, s), 8.17(1H, d), 7.94~7.63(21H, m), 7.49~7.35(7H, m), 7.16(1H,t) 228 δ = 9.08(1H, d), 8.84(1H, d), 8.55(1H, d), 8.44(1H, s), 8.42(1H,d), 8.36(2H, d) 8.17(1H, d), 7.96~7.85(14H, m), 7.75~7.62(6H, m),7.50~7.35(7H, m), 7.25(4H, d), 7.16(1H, t) 229 δ = 9.08(1H, d), 8.84(1H,d), 8.55(1H, d), 8.44(1H, s), 8.42~8.17(10H, m), 7.94~7.85(9H, m),7.75~7.60(8H, m), 7.50~7.35(8H, m), 7.16(1H, t) 234 δ = 9.02(1H, d),8.95(1H, d), 8.55(1H, d), 8.42(1H, d), 8.36(2H, d), 8.19(2H, d),8.06(1H, d), 7.96~7.84(11H, m), 7.75(2H, d), 7.65(2H, t), 7.50~7.35(10H,m), 7.25(2H, d), 7.16(1H, t) 236 δ = 9.02(1H, d), 8.95(1H, d), 8.55(1H,d), 8.42(1H, d), 8.30(2H, d), 8.19(2H, d), 8.06(1H, d), 7.94~7.85(13H,m), 7.75(2H, d), 7.65~7.35(12H, m), 7.16(1H, t) 237 δ = 8.69(2H, d),8.55(1H, d), 8.36(4H, d), 8.20(1H, d), 7.96~7.94(4H, d), 7.85(1H, t),7.70~7.50(12H, m), 7.35(1H, t), 7.16(1H, t) 238 δ = 8.69(2H, d),8.55(1H, d), 8.35(2H, d), 8.30(2H, d), 8.23(1H, s), 8.20(1H, d),7.94(4H, d), 7.70~7.49(12H, m), 7.35(1H, t), 7.16(1H, t) 240 δ =8.69(2H, d), 8.55(1H, d), )8.36(2H, d), 8.20(1H, d), 7.96~7.94(6H, m),7.85(1H, t), 7.70~7.35(15H, m), 7.25(2H, d), 7.16(1H, t) 242 δ =8.69(2H, d), 8.55(1H, d), 8.30(2H, d), 8.23(1H, s), 8.20(1H, d),7.96~7.85(9H, m), 7.70~7.35(15H, m), 7.16(1H, t) 248 δ = 8.97(2H, d),8.68(1H, d), 8.55(1H, d), 8.35~8.20(5H, m), 7.94~7.85(5H, m),7.62~7.50(14H, m), 7.35(1H, t), 7.16(1H, t) 250 δ = 8.97(2H, d),8.89(1H, d), 8.55(1H, d), 8.36~8.29(3H, d), 8.20(1H, d), 7.94(4H, d),7.85(1H, t), 7.70~7.35(17H, m), 7.25(2H, d), 7.16(1H, t) 251 δ =8.97(2H, d), 8.68(1H, d), 8.55(1H, d), 8.35~8.20(7H, m), 7.94(2H, d),7.85(2H, d), 7.75~7.35(17H, m), 7.16(1H, t) 253 δ = 8.97(2H, d),8.68(1H, d), 8.55(1H, d), 8.29(1H, d), 8.20(1H, d), 7.96~7.94(7H, m),7.70~7.35(19H, m), 7.25(4H, d), 7.16(1H, t) 259 δ = 8.69(2H, d),8.55(1H, d), 8.23(1H, s), 8.20(1H, d), 7.94~7.85(11H, m), 7.70~7.49(12H,m), 7.35(1H, t), 7.25(2H, d), 7.16(1H, t) 263 δ = 8.69(2H, d), 8.55(1H,d), 8.20(1H, d), 7.96~7.85(11H, m), 7.70~7.41(17H, m), 7.25(6H, d),7.16(1H, t) 264 δ = 8.69(2H, d), 8.55(1H, d), 8.30(4H, d), 8.23(1H, s),8.20(1H, d), 7.96~7.41(28H, m), 7.25(2H, d), 7.16(1H, t) 267 δ =8.55(1H, d), 8.38(1H, s), 8.36(4H, d), 8.33(2H, s), 8.20(1H, d),7.94(2H, d), 7.85(1H, t), 7.70~7.50(13H, m), 7.35(1H, d), 7.16(1H, t)270 δ = 8.55(1H, d), 8.38(1H, s), 8.36(4H, d), 8.20(1H, d), 7.96(4H, d),7.70~7.35(16H, m), 7.25(2H, d), 7.16(1H, t) 273 δ = 8.55(1H, d) 8.38(1H,s), 8.33(3H, d), 8.20(1H, d), 7.96~7.94(7H, m), 7.70~7.35(18H, m),7.25(4H, d), 7.16(1H, t) 277 δ = 9.60(1H, d), 9.27(1H, s), 8.69(2H, d),8.55(1H, d), 8.30(3H, d), 8.20~8.15(2H, d), 7.96~7.85(7H, m),7.70~7.50(15H, m), 7.35(1H, t), 7.25(2H, d), 7.16(1H, t) 278 δ =9.60(1H, d), 9.27(1H, s), 8.69(2H, d), 8.55(1H, d), 8.37~8.30(5H, m),8.20(1H, d), 7.96~7.85(9H, m), 7.70~7.50(15H, m), 7.35(1H, t),7.25~7.16(5H, m) 282 δ = 9.60(1H, d), 9.27(1H, s), 8.69(2H, d), 8.55(1H,d), 8.37~8.30(3H, d), 8.23(1H, s), 8.20(1H, d), 7.96~7.85(11H, m),7.70~7.49(16H, m), 7.35(1H, t), 7.25(2H, d), 7.16(1H, t) 283 δ =9.02(1H, d), 8.95(1H, d), 8.69(2H, d), 8.55(1H, d), 8.36(2H, d),8.20(1H, d), 8.08(1H, d), 8.06(1H, d), 7.98~7.84(6H, m), 7.70~7.35(18H,m), 7.16(1H, t) 284 δ = 8.69(2H, d), 8.55(1H, d), 8.36(2H, d), 8.20(1H,d), 8.09(1H, d), 7.94~7.50(20H, m), 7.38~7.25(5H, m), 7.16(1H, t),1.69(6H, s) 288 δ = 8.69(2H, d), 8.55(1H, d), 8.36(2H, d), 8.20(1H, d),7.96~7.82(11H, m), 7.70~7.50(9H, m), 7.35(1H, t), 7.25(2H, d), 7.16(1H,t) 290 δ = 8.69(1H, d), 8.55(1H, d), 8.23(1H, s), 8.20(1H, d), 8.12(1H,d), 8.02~7.85(11H, m), 7.70~7.49(10H, m), 7.35(1H, t), 7.25(2H, d),7.16(1H, t) 292 δ = 8.69(2H, d), 8.55(1H, d), 8.20(1H, d),7.96~7.35(25H, m), 7.25(4H, d), 7.16(1H, t) 293 δ = 8.69(2H, d),8.55(1H, d), 8.38(1H, d), 8.20(1H, d), 7.95~7.35(26H, m), 7.25(2H, d),7.16(1H, t) 296 δ = 9.08(1H, d), 8.84(1H, d), 8.69(2H, d), 8.55(1H, d),8.36(2H, d), 8.27~8.20(2H, d), 8.05(1H, s), 7.96~7.85(10H, m),7.70~7.50(13H, m), 7.35(1H, t), 7.25(2H, d), 7.16(1H, t) 299 δ =9.27(1H, s), 8.85(1H, d), 8.69(2H, d), 8.55~8.52(2H, d), 8.23~8.15(3H,m), 7.96~7.85(10H, m), 7.75~7.49(13H, m), 7.35(1H, t), 7.25(2H, d),7.16(1H, t) 300 δ = 8.69(2H, d), 8.55(1H, d), 8.36(2H, d), 8.20(1H, d),8.04(3H, s), 7.96~7.94(4H, d), 7.85(3H, t), 7.70~7.35(20H, m), 7.25(2H,d), 7.16(1H, t) 303 δ = 9.02(1H, d), 8.95(1H, d), 8.69(2H, d), 8.55(1H,d), 8.30~8.20(6H, m), 8.06(1H, d), 7.95~7.35(27H, m), 7.25(2H, d),7.16(1H, t) 304 δ = 9.02((1H, d), 8.95(1H, d), 8.69(2H, d), 8.55(1H, d),8.38(2H, d), 8.20(1H, d), 8.06(1H, d), 7.94~7.41(29H, m), 7.25(2H, d),7.16(1H, t) 305 δ = 9.60(1H, d), 9.27(1H, s), 8.97(2H, d), 8.68(1H, d),8.55(1H, d), 8.38~8.30(7H, m), 8.20(1H, d), 7.94(3H, d), 7.85(1H, t),7.73~7.50(19H, m), 7.35(1H, t), 7.16(1H, t) 306 δ = 9.02(1H, d),8.95(1H, d), 8.69(2H, d), 8.55(1H, d), 8.35(2H, d), 8.23(1H, s),8.20(1H, d), 8.08(1H, d), 8.06(1H, d), 7.98~7.94(3H, d), 8.85~8.84(2H,t), 7.74~7.39(19H, m), 7.16(1H, t) 308 δ = 8.95(1H, d), 8.69(2H, d),8.55(1H, d), 8.36(2H, d), 8.20(3H, d), 8.06(1H, d), 7.96~7.94(4H, m),7.85(1H, d), 7.70~7.50(13H, m), 7.39~7.16(9H, m) 313 δ = 8.55(1H, d),8.35~8.30(7H, m), 8.23(1H, s), 8.20(1H, d), 7.94(3H, d), 7.85(3H, d),7.60~7.35(17H, m), 7.25(2H, d), 7.16(1H, t) 321 δ = 8.55(1H, d),8.23(1H, s), 8.20(1H, d), 7.94~7.85(12H, m), 7.70(1H, t), 7.55~7.49(7H,m), 7.35(1H, t), 7.28(2H, t), 7.16(1H, t) 324 δ = 8.55(1H, d), 8.30(2H,d), 8.23(1H, s), 8.20(1H, d), 7.94~7.85(13H, m), 7.75(2H, d), 7.70(1H,t), 7.55~7.28(10H, m), 7.16(1H, t) 325 δ = 8.55(1H, d), 8.20(1H, d),7.96~7.85(13H, m), 7.75(4H, d), 7.70(1H, t), 7.49~7.28(14H, m), 7.16(1H,t) 332 δ = 8.97(1H, d), 8.55(1H, d), 8.36(2H, d), 8.28~8.20(2H, d),8.12(1H, d), 7.96~7.70(11H, m), 7.50~7.16(15H, m) 336 δ = 8.97(1H, d),8.55(1H, d), 8.30~8.20(7H, m), 8.12(1H, d), 7.94~7.70(15H, m),7.59~7.28(12H, m), 7.16(1H, t) 339 δ = 8.55(1H, d), 8.36(4H, d),8.20(1H, d), 7.96~7.85(11H, m), 7.70(1H, t), 7.50(7H, m), 7.35~7.28(5H,m), 7.16(1H, t) 343 δ = 8.55(1H, d), 8.35~8.30(6H, d), 8.23(1H, s),8.20(1H, d), 7.94~7.86(13H, m), 7.75(3H, t), 7.50~7.28(10H, m), 7.16(1H,t) 345 δ = 8.55(1H, d), 8.20(1H, d), 7.96~7.85(15H, m), 7.75(4H, d),7.70(1H, t), 7.49~7.16(17H, m) 352 δ = 8.55(1H, d), 8.36(2H, d),8.24~8.20(3H, m), 7.96~7.85(7H, m), 7.75(5H, d), 7.50~7.28(12H, m),7.16(1H, t) 353 δ = 8.55(1H, d), 8.35~8.30(4H, d), 8.23~8.20(3H, m),7.94~7.75(13H, m), 7.50~7.28(10H, m), 7.16(1H, t) 363 δ = 8.55(1H, d),8.51(1H, d), 8.23(1H, s), 8.20(1H, d), 8.11(1H, d), 7.94~7.86(12H, m),7.72~7.67(2H, t), 7.55~7.49(7H, m), 7.35~7.28(3H, t), 7.16(1H, t) 365 δ= 8.55(1H, d), 8.35~8.23(4H, m), 8.11(1H, d), 8.03(1H, s), 7.94~7.86(9H,m), 7.75~7.69(3H, m), 7.55~7.49(7H, m), 7.35~7.28(3H, m), 7.16(1H, t)367 δ = 8.55(1H, d), 8.44(1H, d), 8.36(4H, d), 8.06~7.86(10H, m),7.61~7.50(9H, m), 7.35~7.28(3H, m), 7.16(1H, t) 370 δ = 8.80(1H, d),8.71(1H, d), 8.55(1H, d), 8.45(1H, d), 8.30(2H, d), 8.20(2H, d),7.94~7.85(8H, m), 7.70(1, t), 7.56~7.49(2H, t), 7.35~7.28(4H, d),7.16(1H, t) 372 δ = 8.71(2H, d), 8.55(1H, d), 8.33~8.30(4H, d), 8.20(2H,d), 7.94~7.85(8H, m), 7.70(1H, t), 7.55~7.49(4H, m), 7.35~7.29(5H, m),7.16(1H, t) 373 δ = 8.71~8.69(4H, d), 8.55(1H, d), 8.33(2H, d), 8.20(2H,d), 7.94~7.86(12H, m), 7.70(1H, t), 7.55~7.49(4H, m), 7.35~7.28(5H, m),7.16(1H, t) 374 δ = 8.71(2H, d), 8.55(1H, d), 8.33(4H, d), 8.20(2H, d),7.94~7.85(10H, m), 7.73~7.70(2H, t), 7.61~7.49(5H, m), 7.35~7.28(5H, m),7.16(1H, t) 376 δ = 8.55(1H, d), 8.20(1H, d), 8.09(1H, d),7.94~7.70(17H, m), 7.61~7.28(15H, m), 7.16(1H, t) 379 δ = 8.55(1H, d),8.36(2H, d), 8.20(1H, d), 7.96~7.86(11H, m), 7.75~7.70(3H, t),7.50~7.16(17H, m) 380 δ = 8.55(1H, d), 8.35~8.30(4H, d), 8.23~8.20(3H,d), 7.94~7.85(11H, m), 7.75~7.70(3H, t), 7.50~7.28(14H, m), 7.16(1H, t)381 δ = 8.55(1H, d), 8.23(1H, s), 8.20(1H, d), 7.94~7.85(15H, m),7.70(1H, t), 7.55~7.49(7H, m), 7.49~7.25(9H, m), 7.16(1H, t) 382 δ =8.55(1H, d), 8.36(4H, d), 8.20(1H, d), 7.96~7.85(11H, m), 7.70(1H, t),7.50(7H, m), 7.25~7.16(10H, m) 384 δ = 9.00(2H, d), 8.55(1H, d),8.36(4H, d), 8.20(1H, d), 7.96~7.85(11H, m), 7.70(1H, t), 7.61(2H, d),7.50~7.49(7H, m), 7.39~7.28(7H, m), 7.16(1H, t) 388 δ = 8.55~8.52(3H,d), 8.36~8.31(5H, d), 8.20(1H, d), 8.08~8.04(4H, m), 7.94~7.85(8H, m),7.70(2H, d), 7.50(6H, s), 7.35(1H, t), 7.16(1H, t) 391 δ = 9.66(1H, s),8.79(1H, d), 8.54(2H, d), 8.36~8.33(4H, d), 8.20(1H, d), 7.96~7.85(9H,m), 7.75~7.64(7H, m), 7.50~7.35(8H, m), 7.25(2H, d), 7.16(1H, t) 395 δ =9.66(1H, s), 8.85(1H, d), 8.55(3H, d), 8.30~8.20(6H, m), 7.94~7.63(21H,m), 7.49~7.35(7H, m), 7.16(1H, t) 396 δ = 9.02(1H, d), 8.95(1H, d),8.55(1H, d), 8.45(1H, d), 8.36~8.32(3H, d), 8.20(1H, d), 8.06(1H, d),7.96~7.85(13H, m), 7.70(2H, t), 7.52~7.46(8H, m), 7.35~7.25(5H, m),7.16(1H, t) 397 δ = 9.02(1H, d), 8.95(1H, d), 8.55(1H, d), 8.20(1H, d),8.06(1H, d), 7.94~7.84(13H, m), 7.70(1H, t), 7.55~7.49(8H, m),7.35~7.16(8H, m) 398 δ = 9.02(1H, d), 8.95(1H, d), 8.55(1H, d), 8.23(1H,s), 8.20(1H, d), 8.18(1H, s), 8.06(1H, d), 7.94~7.86(13H, m),7.74~7.64(3H, d), 7.55~7.28(12H, m), 7.16(1H, t) 399 δ = 8.69(2H, d),8.55(2H, d), 8.36(4H, d), 8.06~7.94(6H, m), 7.85(2H, d), 7.63~7.50(13H,m), 7.35(1H, t), 7.25(2H, d), 7.16(1H, t) 400 δ = 9.02(1H, d), 8.95(1H,d), 8.69(2H, d), 8.55(1H, d), 8.35(2H, d), 8.23(1H, s), 8.28(1H, d),8.11(1H, d), 8.03(1H, s), 8.06(1H, d), 7.94(1H, d), 7.84(1H, d),7.75~7.46(16H, m), 7.35(1H, t), 7.25(2H, d), 7.16(1H, t) 401 δ =8.69(2H, d), 8.55(1H, d), 8.51(1H, d), 8.23(1H, s), 8.20(1H, d),8.11(1H, d), 7.96~7.90(8H, m), 7.72~7.49(13H, m), 7.35(1H, t), 7.16(1H,t)

TABLE 14 Compound FD-MS 1 m/z = 601.71 (C42H27N5 = 601.22) 2 m/z =600.72 (C43H28N4 = 600.23) 3 m/z = 600.72 (C43H28N4 = 600.23) 4 m/z =677.81 (C48H31N5 = 677.23) 5 m/z = 676.81 (C49H32N4 = 676.26) 6 m/z =676.82 (C49H32N4 = 676.26) 7 m/z = 753.90 (C54H35N5 = 753.28) 8 m/z =752.92 (C55H36N4 = 752.29) 9 m/z = 601.71 (C42H27N5 = 601.22) 10 m/z =599.73 (C44H29N3 = 599.23) 11 m/z = 599.73 (C44H29N3 = 599.23) 12 m/z =675.83 (C50H33N3 = 675.26) 13 m/z = 570.63 (C39H27N2OP = 570.18) 14 m/z= 651.77 (C46H29N5 = 651.24) 15 m/z = 650.78 (C47H30N4-650.24) 16 m/z =650.78 (C47H30N4 = 650.24) 17 m/z = 727.87 (C52H33N5 = 727.27) 18 m/z =726.88 (C53H34N4 = 726.27) 19 m/z = 726.88 (C53H34N4 = 726.27) 20 m/z =803.96 (C58H37N5 = 803.30) 21 m/z = 802.98 (C59H38N4 = 802.31) 22 m/z =651.77 (C46H29N5 = 651.24) 23 m/z = 620.69 (C43H29N2OP = 620.20) 24 m/z= 677.81 (C48H31N5 = 677.25) 25 m/z = 676.82 (C49H32N4 = 676.26) 26 m/z= 676.82 (C49H32N4 = 676.26) 27 m/z = 753.90 (C54H35N5 = 753.28) 28 m/z= 752.91 (C55H36N4 = 752.29) 29 m/z = 752.92 (C55H36N4 = 752.29) 30 m/z= 830.00 (C60H39N5 = 829.31) 31 m/z = 829.01 (C61H40N4 = 828.32) 32 m/z= 829.01 (C61H40N4 = 828.32) 33 m/z = 677.81 (C48H31N5 = 677.25) 34 m/z= 646.73 (C45H31N2OP = 646.21) 35 m/z = 601.71 (C42H27N5 = 601.22) 36m/z = 600.72 (C43H28N4 = 600.23) 37 m/z = 600.72 (C43H28N4 = 600.23) 38m/z = 677.81 (C48H31N5 = 677.25) 39 m/z = 676.82 (C49H32N4 = 676.26) 40m/z = 676.82 (C49H32N4 = 676.26) 41 m/z = 753.90 (C54H35N5 = 753.28) 42m/z = 752.92 (C55H36N4 = 752.29) 43 m/z = 601.71 (C42H27N5 = 601.22) 44m/z = 570.63 (C39H27N2OP = 570.18) 45 m/z = 651.77 (C46H29N5 = 651.24)46 m/z = 650.78 (C47H30N4 = 650.24) 47 m/z = 650.78 (C47H30N4 = 650.24)48 m/z = 727.87 (C52H33N5 = 727.27) 49 m/z = 726.88 (C53H34N4 = 726.27)50 m/z = 726.88 (C53H34N4 = 726.27) 51 m/z = 803.96 (C58H37N5 = 803.30)52 m/z = 802.98 (C59H38N4 = 802.30) 53 m/z = 651.77 (c46H29N5 = 651.24)54 m/z = 650.78 (C47H30N4 = 650.24) 55 m/z = 650.78 (C47H30N4 = 650.24)56 m/z = 727.87 (C52H33N5 = 727.27) 57 m/z = 726.88 (C53H34N4 = 726.27)58 m/z = 726.88 (C53H34N4 = 726.27) 59 m/z = 803.96 (C58H37N5 = 803.30)60 m/z = 802.91 (C59H38N4 = 802.31) 61 m/z = 651.77 (C46H29N5 = 651.24)62 m/z = 650.78 (C47H30N4 = 650.24) 63 m/z = 650.78 (C47H30N4 = 650.24)64 m/z = 803.96 (C58H37N5 = 803.30) 65 m/z = 802.98 (C59H38N4 = 802.31)66 m/z = 751.89 (C54H33N5 = 751.27) 67 m/z = 750.90 (C55H34N4 = 750.27)68 m/z = 750.90 (C55H34N4 = 750.27) 69 m/z = 750.90 (C55H34N4 = 750.27)70 m/z = 753.90 (C54H35N5 = 753.28) 71 m/z = 677.81 (C48H31N5 = 677.25)72 m/z = 676.82 (C49H32N4 = 676.26) 73 m/z = 676.82 (C49H32N4 = 676.26)74 m/z = 676.82 (C49H32N4 = 676.26) 75 m/z = 752.92 (C55H36N4 = 752.29)76 m/z = 752.92 (C55H36N4 = 752.29) 77 m/z = 690.81 (C48H30N6 = 690.25)78 m/z = 766.90 (C54H34N6 = 766.28) 79 m/z = 766.90 (C54H32N6 = 766.28)80 m/z = 689.82 (C49H31N5 = 689.25) 81 m/z = 765.92 (C55H35N5 = 765.28)82 m/z = 765.92 (C55H35N5 = 765.28) 83 m/z = 689.82 (C49H31N5 = 689.25)84 m/z = 765.92 (C55H35N5 = 765.28) 85 m/z = 765.92 (C55H35N5 = 765.28)86 m/z = 765.92 (C55H35N5 = 765.28) 87 m/z = 765.92 (C55H35N5 = 765.28)88 m/z = 717.87 (C51H35N5 = 717.28) 89 m/z = 716.88 (C52H36N4 = 716.29)90 m/z = 716.88 (C52H36N4 = 716.29) 91 m/z = 716.88 (C52H36N4 = 716.29)92 m/z = 793.97 (C57H39N5 = 793.32) 93 m/z = 792.98 (C58H40N4 = 792.32)94 m/z = 792.98 (C58H40N4 = 792.32) 95 m/z = 792.98 (C58H40N4 = 792.32)96 m/z = 626.72 (C43H26N6 = 626.22) 97 m/z = 625.73 (C44H27N5 = 625.22)98 m/z = 625.73 (C44H27N5 = 625.22) 99 m/z = 625.73 (C44H27N5 = 625.22)100 m/z = 702.82 (C49H30N6 = 702.25) 101 m/z = 702.82 (C49H30N6 =702.25) 102 m/z = 701.83 (C50H31N5 = 701.25) 103 m/z = 701.83 (C50H31N5= 701.25) 104 m/z = 777.93 (C56H35N5 = 777.28) 105 m/z = 701.83(C50H31N5 = 701.25) 106 m/z = 776.94 (C57H36N4 = 776.29) 107 m/z =700.84 (C51H32N4 = 700.26) 108 m/z = 753.90 (C54H35N5 = 753.28) 109 m/z= 752.92 (C55H36N4 = 752.29) 110 m/z = 651.77 (C46H29N5 = 651.24) 111m/z = 650.78 (C47H30N4 = 650.24) 112 m/z = 650.78 (C47H30N4 = 650.24)113 m/z = 803.96 (C58H37N5 = 803.30) 114 m/z = 802.98 (C59H38N4 =802.31) 115 m/z = 802.98 (C59H38N4 = 802.31) 116 m/z = 803.96 (C58H37N5= 803.30) 117 m/z = 802.98 (C59H38N4 = 802.31) 118 m/z = 802.98(C59H38N4 = 802.31) 119 m/z = 777.93 (C56H35N5 = 777.28) 120 m/z =879.07 (C65H42N4 = 878.34) 121 m/z = 651.77 (C46H29H5 = 651.24) 122 m/z= 650.78 (C47H30N4 = 650.24) 123 m/z = 650.78 (C47H30N4 = 650.24) 124m/z = 727.87 (C52H33N5 = 727.27) 125 m/z = 726.88 (C53H34N4 = 726.27)126 m/z = 726.88 (C53H34N4 = 726.27) 127 m/z = 803.96 (C58H37N5 =803.30) 128 m/z = 802.98 (C59H38N4 = 802.31) 129 m/z = 651.77 (C46H29N5= 651.24) 130 m/z = 620.69 (C43H29N2OP = 620.20) 131 m/z = 727.87(C52H33N5 = 727.27) 132 m/z = 726.88 (C53H34N4 = 726.27) 133 m/z =726.88 (C53H34N4 = 726.27) 134 m/z = 601.71 (C42H27N5 = 601.22) 135 m/z= 600.72 (C43H28N4 = 600.23) 136 m/z = 600.72 (C43H28N4 = 600.23) 137m/z = 677.81 (C48H31N5 = 677.25) 138 m/z = 676.82 (C49H32N4 = 676.26)139 m/z = 676.82 (C49H32N4 = 676.26) 140 m/z = 753.90 (C54H35N5 =753.28) 141 m/z = 752.92 (C55H36N4 = 752.29) 142 m/z = 601.71 (C42H27N5= 601.22) 143 m/z = 651.77 (C46H29N5 = 651.24) 144 m/z = 650.78(C47H30N4 = 650.24) 145 m/z = 650.78 (C47H30N4 = 650.24) 146 m/z =727.87 (C52H33N5 = 727.27) 147 m/z = 726.88 (C53H34N4 = 726.27) 148 m/z= 726.88 (C53H34N4 = 726.27) 149 m/z = 803.96 (C58H37N5 = 803.30) 150m/z = 802.98 (C59H38N4 = 802.31) 151 m/z = 651.77 (C46H29N5 = 651.24)152 m/z = 548.69 (C39H24N4 = 548.20) 153 m/z = 677.81 (C48H31N5 =677.25) 154 m/z = 676.82 (C49H32N4 = 676.26) 155 m/z = 676.82 (C49H32N4= 676.26) 156 m/z = 624.74 (C45H28N4 = 624.23) 157 m/z = 700.84(C51H32N4 = 700.26) 158 m/z = 700.84 (C51H32N4 = 700.26) 159 m/z =830.00 (C60H39N5 = 829.32) 160 m/z = 829.01 (C61H40N4 = 828.32) 161 m/z= 677.81 (C48H31N5 = 677.25) 162 m/z = 675.83 (C50H33N3 = 675.26) 163m/z = 751.93 (C56H37N3 = 751.29) 164 m/z = 646.73 (C45H31N2OP = 646.21)165 m/z = 601.71 (C42H27N5 = 601.22) 166 m/z = 600.72 (C43H28N4 =600.23) 167 m/z = 600.72 (C43H28N4 = 600.23) 168 m/z = 677.81 (C48H31N5= 677.25) 169 m/z = 676.82 (C49H32N4 = 676.26) 170 m/z = 676.82(C49H32N4 = 676.26) 171 m/z = 753.90 (C54H35N5 = 753.28) 172 m/z =752.92 (C55H36N4 = 752.29) 173 m/z = 601.71 (C42H27N5 = 601.22) 174 m/z= 599.73 (C44H29N3 = 599.23) 175 m/z = 599.73 (C44H29N3 = 599.23) 176m/z = 675.83 (C50H33N3 = 675.26) 177 m/z = 675.83 (C50H33N3 = 675.26)178 m/z = 570.63 (C39H27N2OP = 570.18) 179 m/z = 651.77 (C46H29N5 =651.24) 180 m/z = 650.78 (C47H30N4 = 650.24) 181 m/z = 650.78 (C47H30N4= 650.24) 182 m/z = 727.87 (C52H33N5 = 727.27) 183 m/z = 726.88(C53H34N4 = 726.27) 184 m/z = 726.88 (C53H34N4 = 726.27) 185 m/z =816.96 (C58H36N6 = 816.30) 186 m/z = 816.96 (C58H36N6 = 816.30) 187 m/z= 893.06 (C64H40N6 = 892.33) 188 m/z = 651.77 (C46H29N5 = 651.24) 189m/z = 650.78 (C47H30N4 = 650.24) 190 m/z = 650.78 (C47H30N4 = 650.24)191 m/z = 817.95 (C58H35N5O = 817.28) 192 m/z = 816.96 (C59H36N4O =816.28) 193 m/z = 816.96 (C59H36N4O = 816.28) 194 m/a = 651.77 (C46H29N5= 651.24) 195 m/z = 650.78 (C47H30N4 = 650.24) 196 m/z = 650.78(C47H30N4 = 650.24) 197 m/z = 727.87 (C52H33N5 = 727.27) 198 m/z =726.88 (C53H34N4 = 726.27) 199 m/z = 726.88 (C53H34N4 = 726.27) 200 m/z= 834.01 (C58H35N5S = 833.26) 201 m/z = 833.02 (C59H36N4S = 832.26) 202m/a = 756.92 (C53H32N4S = 756.23) 203 m/z = 691.79 (C48H29N5O = 691.23)204 m/z = 691.79 (C48H29N4O = 691.23) 205 m/z = 766.90 (C55H34N4O =766.27) 206 m/z = 766.90 (C55H34N4O = 766.27) 207 m/z = 701.83 (C50H31N5= 701.25) 208 m/z = 700.84 (C51H32N4 = 700.26) 209 m/z = 707.85(C48H29N5S = 707.21) 210 m/z = 706.86 (C49H30N4S = 706.21) 211 m/z =782.96 (C55H34N4S = 782.25) 212 m/z = 782.96 (C55H34N4S = 782.25) 213m/z = 725.85 (C52H31N5 = 725.25) 214 m/z = 724.86 (C53H32N4 = 724.26)215 m/z = 701.83 (C50H31N5 = 701.25) 216 m/z = 700.84 (C51H32N4 =700.26) 217 m/z = 700.84 (C51H32N4 = 700.26) 218 m/z = 777.93 (C56H35N5= 777.28) 219 m/z = 776.94 (C57H36N4 = 776.29) 220 m/z = 776.94(C57H36N4 = 776.29) 221 m/z = 854.02 (C62H39N5 = 853.32) 222 m/z =853.04 (C63H40N4 = 852.32) 223 m/z = 701.83 (C50H31N5 = 701.25) 224 m/z= 670.75 (C47H31N2OP = 670.21) 225 m/z = 777.93 (C56H35N5 = 777.28) 226m/z = 776.94 (C57H36N4 = 776.29) 227 m/z = 827.00 (C61H38N4 = 826.31)228 m/z = 854.02 (C62H39N5 = 853.32) 229 m/z = 853.04 (C63H40N4 =852.32) 230 m/z = 903.10 (C67H42N4 = 902.34) 231 m/z = 854.02 (C62H39N5= 853.32) 232 m/z = 853.04 (C63H40N4 = 852.32) 233 m/z = 777.93(C56H35N5 = 777.28) 234 m/z = 803.96 (C58H37N5 = 803.30) 235 m/z =802.98 (C59H38N4 = 802.31) 236 m/z = 802.98 (C59H38N4 = 802.31) 237 m/z= 601.71 (C42H27N5 = 601.22) 238 m/z = 600.72 (C43H28N4 = 600.23) 239m/z = 600.72 (C43H28N4 = 600.23) 240 m/z = 677.81 (C48H31N5 = 677.25)241 m/z = 676.82 (C49H32N4 = 676.26) 242 m/z = 676.82 (C49H32N4 =676.26) 243 m/z = 753.90 (C54H35N4 = 753.28) 244 m/z = 752.92 (C55H36N4= 752.29) 245 m/z = 601.71 (C42H27N4 = 601.22) 246 m/z = 570.63(C39H27N2OP = 570.18) 247 m/z = 651.77 (C46H29N5 = 651.24) 248 m/z =650.78 (C47H30N4 = 650.24) 249 m/z = 650.78 (C47H30N4 = 650.24) 250 m/z= 727.87 (C52H33N5 = 727.27) 251 m/z = 726.88 (C53H34N4 = 726.27) 252m/z = 726.88 (C53H34N4 = 726.27) 253 m/z = 803.96 (C58H37N5 = 803.30)254 m/z = 802.98 (C59H38N4 = 802.31) 255 m/z = 651.77 (C46H29N5 =651.24) 256 m/z = 620.69 (C43H29N2OP = 620.20) 257 m/z = 677.81(C48H31N5 = 677.25) 258 m/z = 676.82 (C49H32N4 = 676.26) 259 m/z =676.82 (C49H32N4 = 676.26) 260 m/z = 753.90 (C54H35N5 = 753.28) 261 m/z= 752.92 (C55H36N4 = 752.29) 262 m/z = 752.29 (C55H36N4 = 752.29) 263m/z = 830.00 (C60H39N5 = 829.32) 264 m/z = 829.01 (C61H40N4 = 828.32)265 m/z = 677.81 (C48H31N5 = 677.25) 266 m/z = 646.73 (C45H31N2OP =646.21) 267 m/z = 601.71 (C42H27N5 = 601.22) 268 m/z = 600.72 (C43H28N4= 600.23) 269 m/z = 600.72 (C43H28N4 = 600.23) 270 m/z = 677.81(C48H31N5 = 677.25) 271 m/z = 676.82 (C49H32N4 = 676.26) 272 m/z =676.82 (C49H32N4 = 676.26) 273 m/z = 753.90 (C54H35N5 = 753.28) 274 m/z= 752.92 (C55H36N4 = 752.29) 275 m/z = 601.71 (C42H27N5 = 601.22) 276m/z = 570.63 (C39H27N2OP = 570.18) 277 m/z = 827.99 (C60H37N5 = 827.30)278 m/z = 904.08 (C66H41N5 = 903.33) 279 m/z = 904.08 (C66H41N5 =903.33) 280 m/z = 827.00 (C61H38N4 = 826.31) 281 m/z = 903.10 (C67H42N4= 902.32) 282 m/z = 903.10 (C67H42N4 = 902.23) 283 m/z = 817.95(C58H35N5O = 817.28) 284 m/z = 793.97 (C57H39N5 = 793.32) 285 m/z =792.98 (C58H40N4 = 792.32) 286 m/z = 792.98 (C58H40N4 = 792.32) 287 m/z= 792.98 (C58H40N4 = 792.32) 288 m/z = 702.82 (C49H30N6 = 702.25) 289m/z = 701.83 (C50H31N5 = 701.25) 290 m/z = 701.83 (C50H31N5 = 701.25)291 m/z = 701.83 (C50H31N5 = 701.25) 292 m/z = 778.91 (C55H34N6 =778.28) 293 m/z = 778.91 (C55H34N6 = 778.28) 294 m/z = 777.93 (C56H35N5= 777.28) 295 m/z = 777.93 (C56H35N5 = 777.28) 296 m/z = 854.02(C62H39N5 = 853.32) 297 m/z = 777.93 (C56H35N5 = 777.28) 298 m/z =853.04 (C63H40N4 = 852.32) 299 m/z = 776.94 (C57H36N4 = 776.29) 300 m/z= 830.00 (C60H39N5 = 829.32) 301 m/z = 829.01 (C61H40N4 = 828.32) 302m/z = 880.06 (C64H41N5 = 879.33) 303 m/z = 879.07 (C65H42N4 = 878.34)304 m/z = 880.06 (C64H41N5 = 879.33) 305 m/z = 878.05 (C64H39N5 =877.32) 306 m/z = 816.96 (C59H36N4O = 816.28) 307 m/z = 893.06(C65H40N4O = 829.32) 308 m/z = 894.05 (C64H39N5O = 893.31) 309 m/z =601.71 (C42H27N5 = 601.22) 310 m/z = 600.72 (C43H28N4 = 600.23) 311 m/z= 600.72 (C43H28N4 = 600.23) 312 m/z = 677.81 (C48H31N5 = 677.25) 313m/z = 752.92 (Cm55H36N4 = 752.29) 314 m/z = 752.92 (c55H36N4 = 752.29)315 m/z = 753.90 C(54H35N5 = 753.28) 316 m/z = 752.92 (C55H36N4 =752.29) 317 m/z = 677.82 (C48H31N5 = 677.25) 318 m/z = 570.63(C39H27N2OP = 570.18) 319 m/z = 601.71 (C42H27N5 = 601.22) 320 m/z =600.72 (C43H28N4 = 600.23) 321 m/z = 600.72 (C43H28N4 = 600.23) 322 m/z= 677.81 (C48H31N5 = 677.25) 323 m/z = 676.82 (C49H32N4 = 676.26) 324m/z = 676.82 (C49H32N4 = 676.26) 325 m/z = 753.90 (C54H35N5 = 753.28)326 m/z = 752.92 (C55H36N4 = 752.29) 327 m/z = 601.71 (C42H27N5 =601.22) 328 m/z = 570.63 (C39H27N2OP = 570.18) 329 m/z = 651.77(C46H29N5 = 651.24) 330 m/z = 650.78 (C47H30N4 = 650.24) 331 m/z =650.78 (C47H30N4 = 650.24). 332 m/z = 727.87 (C52H33N5 = 727.27) 333 m/z= 726.88 (C53H34N4 = 726.27) 334 m/z = 726.88 (C53H34N4 = 726.27) 335m/z = 803.96 (C58H37N5 = 803.30) 336 m/z = 802.98 (C59H38N4 = 802.31)337 m/z = 651.77 (C46H29N5 = 651.24) 338 m/z = 620.69 (C43H29N2OP =620.20) 339 m/z = 677.81 (C548H31N5 = 677.25) 340 m/z = 676.82 (C49H32N4= 676.26) 341 m/z = 676.82 (C49H32N4 = 676.26) 342 m/z = 753.90(C54H35N5 = 753.28) 343 m/z = 752.92 (C55H36NN4 = 752.29) 344 m/z =752.92 (C55H36N4 = 752.29) 345 m/z = 830.00 (C60H39N5 = 829.32) 346 m/z= 829.01 (C61H40N4 = 828.32) 347 m/z = 677.81 (C48H31N5 = 677.25) 348m/z = 646.73 (C45H31N2OP = 646.21) 349 m/z = 601.71 (C42H27N5 = 601.22)350 m/z = 600.72 (C43H28N4 = 600.23) 351 m/z = 600.72 (C43H28N4 =600.23) 352 m/z = 677.81 (C48H31N5 = 677.25) 353 m/z = 676.82 (C49H32N4= 676.26) 354 m/z = 676.82 (C49H32N4 = 676.26) 355 m/z = 753.90(C54H35N5 = 753.28) 356 m/z = 752.92 (C55H36N4 = 752.29) 357 m/z =601.71 (C42H27N5 = 601.22) 358 m/z = 599.73 (C44H29N3 = 599.23) 359 m/z= 599.73 (C44H29N3 = 599.23) 360 m/z = 570.63 (C39H27N2OP = 570.18) 361m/z = 651.77 (C46H29N5 = 651.24) 362 m/z = 650.78 (C47H30N4 = 650.24)363 m/z = 650.78 (C47H30N4 = 650.24) 364 m/z = 651.77 (C46H29N5 =651.24) 365 m/z = 650.78 (C47H30N4 = 6050.24) 366 m/z = 650.78 (C47H30N4= 650.24) 367 m/z = 651.77 (C46H29N5 = 651.24) 368 m/z = 650.78(C47H30N4 = 650.24) 369 m/z = 650.78 (C47H30N4 = 650.24) 370 m/z =548.64 (C39H24N4 = 548.20) 371 m/z = 624.74 (C45H28N4 = 624.23) 372 m/z= 624.74 (C45H28N4 = 624.23) 373 m/z = 700.84 (C51H32N4 = 700.26) 374m/z = 700.84 (C51H32N4 = 700.26) 375 m/z = 760.94 (C58H36N2 = 760.28)376 m/z = 760.94 (C58H36N2 = 760.28) 377 m/z = 811.00 (C62H38N2 =810.30) 378 m/z = 752.92 (C55H36N4 = 752.29) 379 m/z = 853.90 (C54H35N5= 753.28) 380 m/z = 752.92 (C55H36N4 = 752.29) 381 m/z = 752.92(C55H36N4 = 752.29) 382 m/z = 753.90 (C54H35N5 = 753.28) 383 m/z =802.98 (C59H38N4 = 802.31) 384 m/z = 803.96 (C58H37N5 = 803.30) 385 m/z= 677.81 (C48H31N5 = 677.25) 386 m/z = 725.89 (C54H35N3 = 725.28) 387m/z = 725.89 (C54H35N3 = 725.28) 388 m/z = 725.85 (C52H31N5 = 725.25)389 m/z = 726.88 (C53H34N4 = 726.27) 390 m/z = 724.86 (C53H32N4 =724.26) 391 m/z = 827.99 (C60H37N5 = 827.30) 392 m/z = 827.00 (C61H38N4= 826.31) 393 m/z = 827.00 (C61H38N4 = 826.31) 394 m/z = 854.02(C62H39N5 = 853.32) 395 m/z = 853.04 (C63H40N4 = 852.32) 396 m/z =910.11 (C64H39N5S = 909.29) 397 m/z = 815.98 (C59H37N5 = 815.30) 398 m/z= 843.04 (C62H42N4 = 842.34) 399 m/z = 727.87 (C52H33N5 = 727.27) 400m/z = 776.94 (C57H36N4 = 776.29) 401 m/z = 650.78 (C47H30N4 = 650.24)

<Experimental Example 1> Manufacture of Organic Light Emitting Device

1) Manufacture of Organic Light Emitting Device

A transparent ITO electrode thin film obtained from glass for an OLED(manufactured by Samsung-Corning Co., Ltd.) was ultrasonic cleaned usingtrichloroethylene, acetone, ethanol and distilled water consecutivelyfor 5 minutes each, stored in isopropanol, and used.

Next, an ITO substrate was installed in a substrate folder of a vacuumdepositor, and the following4,4′,4″-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) wasintroduced to a cell in the vacuum depositor.

Subsequently, the chamber was evacuated until the degree of vacuumtherein reached 10⁻⁶ torr, and then 2-TNATA was evaporated by applying acurrent to the cell to deposit a hole injection layer having a thicknessof 600 Å on the ITO substrate.

To another cell of the vacuum depositor, the followingN,N′-bis(α-naphthyl)-N,N′-diphenyl-4,4′-diamine (NPB) was introduced,and evaporated by applying a current to the cell to deposit a holetransfer layer having a thickness of 300 Å on the hole injection layer.

After forming the hole injection layer and the hole transfer layer asabove, a blue light emitting material having a structure as below wasdeposited thereon as a light emitting layer. Specifically, in one sidecell in the vacuum depositor, H1, a blue light emitting host material,was vacuum deposited to a thickness of 200 Å, and D1, a blue lightemitting dopant material, was vacuum deposited thereon by 5% withrespect to the host material.

Subsequently, one of compounds described in Table 15 was deposited to athickness of 300 Å as an electron transfer layer.

As an electron injection layer, lithium fluoride (LiF) was deposited toa thickness of 10 Å, and an Al cathode was employed to have a thicknessof 1,000 Å to manufacture an OLED.

Meanwhile, all the organic compounds required to manufacture the OLEDwere vacuum sublimation purified under 10⁻⁶ torr to 10⁻⁸ torr by eachmaterial to be used in the OLED manufacture.

Results of measuring a driving voltage, light emission efficiency, acolor coordinate (CIE) and a lifetime of the blue organic light emittingdevice manufactured according to the present disclosure are as shown inTable 15.

TABLE 15 Light Driving Emission Voltage Efficiency CIE Lifetime Compound(V) (cd/A) (x, y) (T95) Comparative E1 5.70 6.00 (0.134, 0.102) 20Example 1 Comparative A 5.33 4.21 (0.134, 0.100) 12 Example 2Comparative B 5.31 4.10 (0.134, 0.100) 8 Example 3 Comparative C 5.264.98 (0.134, 0.100) 9 Example 4 Example 1 1 5.45 6.21 (0.134, 0.101) 37Example 2 2 5.44 6.22 (0.134, 0.102) 34 Example 3 4 5.62 5.95 (0.134,0.103) 42 Example 4 6 4.98 6.44 (0.134, 0.100) 40 Example 5 7 5.62 6.38(0.134, 0.100) 35 Example 6 8 4.72 6.20 (0.134, 0.102) 48 Example 7 165.45 6.44 (0.134, 0.103) 33 Example 8 21 5.44 6.34 (0.134, 0.102) 36Example 9 26 5.62 6.20 (0.134, 0.101) 39 Example 10 28 5.40 6.12 (0.134,0.103) 44 Example 11 31 5.60 6.21 (0.134, 0.102) 43 Example 12 33 5.456.22 (0.134, 0.101) 37 Example 13 35 4.98 6.38 (0.134, 0.101) 42 Example14 37 5.62 6.20 (0.134, 0.100) 45 Example 15 39 4.72 6.12 (0.134, 0.100)43 Example 16 41 4.91 6.21 (0.134, 0.101) 41 Example 17 42 4.98 6.22(0.134, 0.100) 40 Example 18 45 5.62 5.95 (0.134, 0.100) 33 Example 1959 5.44 6.13 (0.134, 0.102) 25 Example 20 65 5.38 6.38 (0.134, 0.101) 39Example 21 66 5.38 6.20 (0.134, 0.103) 40 Example 22 68 5.39 6.25(0.134, 0.102) 41 Example 23 70 4.96 6.21 (0.134, 0.101) 37 Example 2473 4.91 6.22 (0.134, 0.102) 33 Example 25 74 4.91 6.12 (0.134, 0.101) 42Example 26 77 4.98 6.51 (0.134, 0.101) 39 Example 27 78 5.62 6.21(0.134, 0.100) 41 Example 28 88 5.39 5.95 (0.134, 0.101) 34 Example 2993 5.38 5.85 (0.134, 0.101) 35 Example 30 96 5.38 6.38 (0.134, 0.101) 39Example 31 100 5.38 6.20 (0.134, 0.103) 40 Example 32 101 5.39 6.42(0.134, 0.102) 43 Example 33 104 4.96 6.21 (0.134, 0.101) 37 Example 34105 4.91 6.22 (0.134, 0.102) 33 Example 35 108 4.91 6.12 (0.134, 0.101)37 Example 36 115 5.38 6.38 (0.134, 0.101) 39 Example 37 117 5.38 6.20(0.134, 0.103) 40 Example 38 120 5.39 6.62 (0.134, 0.102) 43 Example 39131 4.96 6.21 (0.134, 0.101) 37 Example 40 132 4.91 6.22 (0.134, 0.102)33 Example 41 134 4.91 6.12 (0.134, 0.101) 42 Example 42 135 4.98 6.51(0.134, 0.101) 39 Example 43 137 5.62 6.21 (0.134, 0.100) 41 Example 44139 5.39 5.95 (0.134, 0.101) 34 Example 45 141 5.10 6.88 (0.134, 0.100)41 Example 46 143 5.38 6.38 (0.134, 0.101) 39 Example 47 148 5.38 6.20(0.134, 0.103) 40 Example 48 149 5.11 6.62 (0.134, 0.102) 43 Example 49155 4.95 6.22 (0.134, 0.100) 41 Example 50 157 4.98 6.92 (0.134, 0.100)40 Example 51 159 5.62 5.98 (0.134, 0.100) 39 Example 52 161 4.75 6.53(0.134, 0.102) 40 Example 53 165 4.72 6.35 (0.134, 0.102) 42 Example 54168 4.91 6.93 (0.134, 0.100) 45 Example 55 169 4.93 6.95 (0.134, 0.100)40 Example 56 187 4.98 6.21 (0.134, 0.100) 40 Example 57 192 5.62 5.98(0.134, 0.100) 34 Example 58 195 5.31 6.53 (0.134, 0.102) 35 Example 59203 4.79 6.55 (0.134, 0.102) 48 Example 60 205 5.40 6.13 (0.134, 0.101)39 Example 61 209 5.44 6.04 (0.134, 0.100) 41 Example 62 212 5.39 6.01(0.134, 0.101) 34 Example 63 213 4.96 6.88 (0.134, 0.100) 45 Example 64218 4.95 6.95 (0.134, 0.100) 41 Example 65 219 4.98 6.22 (0.134, 0.100)40 Example 66 222 5.62 5.98 (0.134, 0.100) 33 Example 67 228 4.75 6.53(0.134, 0.102) 40 Example 68 229 5.40 6.12 (0.134, 0.101) 39 Example 69234 5.44 6.21 (0.134, 0.100) 41 Example 70 236 5.39 6.20 (0.134, 0.101)36 Example 71 237 5.39 6.88 (0.134, 0.100) 45 Example 72 238 5.21 6.93(0.134, 0.100) 43 Example 73 240 5.13 6.95 (0.134, 0.100) 41 Example 74242 5.05 6.22 (0.134, 0.100) 40 Example 75 248 4.91 5.98 (0.134, 0.100)33 Example 76 250 4.72 6.53 (0.134, 0.102) 48 Example 77 251 5.40 6.12(0.134, 0.101) 39 Example 78 253 5.43 6.53 (0.134, 0.102) 48 Example 79259 5.33 6.53 (0.134, 0.102) 48 Example 80 263 4.91 6.98 (0.134, 0.100)43 Example 81 264 4.91 6.12 (0.134, 0.100) 35 Example 82 267 4.98 6.22(0.134, 0.100) 40 Example 83 270 5.62 5.98 (0.134, 0.100) 38 Example 84273 4.72 6.53 (0.134, 0.102) 48 Example 85 277 4.72 6.33 (0.134, 0.102)41 Example 86 278 4.63 6.53 (0.134, 0.102) 48 Example 87 282 4.91 6.82(0.134, 0.100) 43 Example 88 283 4.99 6.95 (0.134, 0.100) 41 Example 89284 4.98 6.22 (0.134, 0.100) 40 Example 90 288 5.62 5.98 (0.134, 0.100)33 Example 91 290 5.43 6.53 (0.134, 0.102) 41 Example 92 292 4.88 6.89(0.134, 0.102) 42 Example 93 293 5.40 6.12 (0.134, 0.101) 39 Example 94296 5.41 5.89 (0.134, 0.100) 41 Example 95 299 5.39 6.01 (0.134, 0.101)32 Example 96 300 4.63 6.53 (0.134, 0.102) 48 Example 97 303 4.91 6.82(0.134, 0.100) 43 Example 98 304 4.72 6.53 (0.134, 0.102) 38 Example 99305 4.91 6.78 (0.134, 0.100) 43 Example 100 306 4.90 6.95 (0.134, 0.100)41 Example 101 308 4.98 6.22 (0.134, 0.100) 40 Example 102 313 5.62 5.98(0.134, 0.100) 33 Example 103 321 5.21 6.03 (0.134, 0.101) 33 Example104 324 5.39 6.01 (0.134, 0.101) 32 Example 105 325 5.33 6.04 (0.134,0.101) 33 Example 106 332 4.91 6.93 (0.134, 0.100) 43 Example 107 3364.77 6.95 (0.134, 0.100) 41 Example 108 339 4.98 6.22 (0.134, 0.100) 40Example 109 343 5.03 5.98 (0.134, 0.100) 39 Example 110 345 4.71 6.51(0.134, 0.102) 41 Example 111 352 4.72 6.53 (0.134, 0.102) 48 Example112 353 4.74 6.59 (0.134, 0.102) 45 Example 113 363 5.42 6.13 (0.134,0.101) 39 Example 114 365 4.72 6.53 (0.134, 0.102) 38 Example 115 3674.91 6.78 (0.134, 0.100) 43 Example 116 370 5.44 5.89 (0.134, 0.100) 41Example 117 372 5.36 6.01 (0.134, 0.101) 32 Example 118 373 4.96 6.82(0.134, 0.100) 45 Example 119 374 4.91 6.93 (0.134, 0.100) 43 Example120 376 4.95 6.95 (0.134, 0.100) 41 Example 121 379 5.34 6.11 (0.134,0.101) 38 Example 122 380 4.86 6.76 (0.134, 0.100) 45 Example 123 3814.94 6.73 (0.134, 0.102) 42 Example 124 382 4.91 6.55 (0.134, 0.100) 46Example 125 384 5.31 6.29 (0.134, 0.100) 42 Example 126 388 5.22 6.11(0.134, 0.100) 35 Example 127 391 5.33 6.24 (0.134, 0.102) 41 Example128 395 5.31 6.57 (0.134, 0.102) 46 Example 129 396 4.72 6.53 (0.134,0.102) 35 Example 130 397 4.79 6.55 (0.134, 0.102) 48 Example 131 3985.40 6.13 (0.134, 0.101) 39 Example 132 399 5.12 5.89 (0.134, 0.100) 41Example 133 400 5.31 6.01 (0.134, 0.101) 34 Example 134 401 5.11 6.88(0.134, 0.100) 45

As seen from the results of Table 15, the organic light emitting deviceusing the electron transfer layer material of the blue organic lightemitting device of the present disclosure had a lower driving voltage,and significantly improved light emission efficiency and lifetimecompared to Comparative Example 1.

In addition, it was identified that light emission efficiency andlifetime were more superior compared to Comparative Example 2 toComparative Example 4. Particularly, it can be seen that Compounds B andC of Comparative Examples 3 and 4 had the core structure of the presentapplication substituted with one substituent. It was identified that,when substituted with one substituent, thermal stability was reducedcompared to the compound substituted with two like the heterocycliccompound of Chemical Formula 1 of the present application, and alifetime decreased particularly.

<Experimental Example 2> Manufacture of Organic Light Emitting Device

1) Manufacture of Organic Light Emitting Device

A transparent ITO electrode thin film obtained from glass for an OLED(manufactured by Samsung-Corning Co., Ltd.) was ultrasonic cleaned usingtrichloroethylene, acetone, ethanol and distilled water consecutivelyfor 5 minutes each, stored in isopropanol, and used.

Next, an ITO substrate was installed in a substrate folder of a vacuumdepositor, and the following4,4′,4″-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) wasintroduced to a cell in the vacuum depositor.

Subsequently, the chamber was evacuated until the degree of vacuumtherein reached 10⁻⁶ torr, and then 2-TNATA was evaporated by applying acurrent to the cell to deposit a hole injection layer having a thicknessof 600 Å on the ITO substrate.

To another cell of the vacuum depositor, the followingN,N′-bis(α-naphthyl)-N,N′-diphenyl-4,4′-diamine (NPB) was introduced,and evaporated by applying a current to the cell to deposit a holetransfer layer having a thickness of 300 Å on the hole injection layer.

After forming the hole injection layer and the hole transfer layer asabove, a blue light emitting material having a structure as below wasdeposited thereon as a light emitting layer. Specifically, in one sidecell in the vacuum depositor, H1, a blue light emitting host material,was vacuum deposited to a thickness of 200 Å, and D1, a blue lightemitting dopant material, was vacuum deposited thereon to 5% withrespect to the host material.

Subsequently, a compound of the following structural formula E1 wasdeposited to a thickness of 300 Å as an electron transfer layer.

As an electron injection layer, lithium fluoride (LiF) was deposited toa thickness of 10 Å, and an Al cathode was employed to have a thicknessof 1,000 Å to manufacture an OLED.

Meanwhile, all the organic compounds required to manufacture the OLEDwere vacuum sublimation purified under 10⁻⁶ torr to 10⁻⁸ torr by eachmaterial to be used in the OLED manufacture.

An electroluminescent device was manufactured in the same manner as inExperimental Example 2 except that, after forming the electron transferlayer E1 to a thickness of 250 Å, a hole blocking layer was formed onthe electron transfer layer to a thickness of 50 Å using a compoundpresented in the following Table 16.

Results of measuring a driving voltage, light emission efficiency, acolor coordinate (CIE) and a lifetime of the blue organic light emittingdevice manufactured according to the present disclosure are as shown inTable 16.

TABLE 16 Light Driving Emission Voltage Efficiency CIE Lifetime Compound(V) (cd/A) (x, y) (T95) Comparative — 5.51 5.94 (0.134, 0.100) 31Example 5 Comparative A 5.21 4.12 (0.134, 0.101) 12 Example 6Comparative B 5.33 4.01 (0.134, 0.100) 11 Example 7 Comparative C 5.314.01 (0.134, 0.100) 11 Example 8 Example 135 2 5.14 6.89 (0.134, 0.102)54 Example 136 8 5.34 6.58 (0.134, 0.101) 44 Example 137 68 5.38 6.51(0.134, 0.103) 47 Example 138 77 5.11 6.75 (0.134, 0.102) 46 Example 139104 5.42 6.21 (0.134, 0.101) 54 Example 140 108 5.13 6.63 (0.134, 0.102)52 Example 141 120 5.05 6.66 (0.134, 0.101) 49 Example 142 205 5.42 6.13(0.134, 0.101) 41 Example 143 212 5.14 6.89 (0.134, 0.102) 54 Example144 213 5.34 6.58 (0.134, 0.101) 44 Example 145 273 5.38 6.51 (0.134,0.103) 47 Example 146 277 5.11 6.75 (0.134, 0.102) 46 Example 147 2885.32 6.25 (0.134, 0.101) 55 Example 148 388 5.14 6.46 (0.134, 0.102) 51Example 149 391 5.04 6.62 (0.134, 0.101) 55 Example 150 395 5.32 6.25(0.134, 0.101) 55

As seen from the results of Table 16, the organic light emitting deviceusing the hole blocking layer material of the blue organic lightemitting device of the present disclosure had a lower driving voltage,and significantly improved light emission efficiency and lifetimecompared to Comparative Example 5. In addition, light emissionefficiency and lifetime were significantly improved compared toComparative Example 6 to Comparative Example 8. Particularly, it can beseen that Compounds B and C of Comparative Examples 7 and 8 had the corestructure of the present application substituted with one substituent.It was identified that, when substituted with one substituent, thermalstability was reduced compared to the compound substituted with two likethe heterocyclic compound of Chemical Formula 1 of the presentapplication, and a lifetime decreased particularly.

Such a reason is due to the fact that the compound of Chemical Formula 1of the present application is a bipolar type having both a p-type and ann-type, and is capable of blocking hole leakage and effectively trappingexcitons in the light emitting layer.

<Experimental Example 3> Manufacture of Organic Light Emitting Device

1) Manufacture of Organic Light Emitting Device

A glass substrate on which ITO was coated as a thin film to a thicknessof 1500 Å was cleaned with distilled water ultrasonic waves. After thecleaning with distilled water was finished, the substrate was ultrasoniccleaned with solvents such as acetone, methanol and isopropyl alcohol,then dried, and UVO treatment was carried out for 5 minutes in a UVcleaner using UV. After that, the substrate was transferred to a plasmacleaner (PT), and plasma treatment was carried out under vacuum for ITOwork function and remaining film removal, and the substrate wastransferred to a thermal deposition apparatus for organic deposition.

On the transparent ITO electrode (anode), an organic material was formedin a 2 stack white organic light emitting device (WOLED) structure. Asfor the first stack, TAPC was thermal vacuum deposited to a thickness of300 Å first to form a hole transfer layer. After forming the holetransfer layer, a light emitting layer was thermal vacuum depositedthereon as follows. The light emitting layer was deposited to 300 Å bydoping FIrpic to TCz1, a host, by 8% as a blue phosphorescent dopant.After forming an electron transfer layer to 400 Å using TmPyPB, a chargegeneration layer was formed to 100 Å by doping Cs₂C03 to the compoundlisted in the following Table 17 by 20%.

As for the second stack, MoO₃ was thermal vacuum deposited to athickness of 50 Å first to form a hole injection layer. A hole transferlayer, a common layer, was formed by doping MoO₃ to TAPC by 20% to 100 Åand depositing TAPC to 300 Å. A light emitting layer was depositedthereon to 300 Å by doping Ir(ppy)₃, a green phosphorescent dopant, toTCz1, a host, by 8%, and an electron transfer layer was formed to 600 Åusing TmPyPB. Lastly, an electron injection layer was formed on theelectron transfer layer by depositing lithium fluoride (LiF) to athickness of 10 Å, and then a cathode was formed on the electroninjection layer by depositing an aluminum (Al) cathode to a thickness of1,200 Å to manufacture an organic light emitting device.

Meanwhile, all the organic compounds required to manufacture the OLEDwere vacuum sublimation purified under 10⁻⁶ torr to 10⁻⁸ torr by eachmaterial to be used in the OLED manufacture.

Results of measuring a driving voltage, light emission efficiency, acolor coordinate (CIE) and a lifetime (T95) of the white organic lightemitting device manufactured according to the present disclosure are asshown in the following Table 17.

TABLE 17 Light Driving Emission Voltage Efficiency CIE Lifetime Compound(V) (cd/A) (x, y) (T95) Comparative TmPyPB 8.57 57.61 (0.212, 0.433) 22Example 9 Comparative BBQB 8.43 58.11 (0.220, 0.429) 22 Example 10Comparative TBQB 8.47 58.90 (0.222, 0.430) 26 Example 11 Comparative A7.21 41.11 (0.201, 0.398) 9 Example 12 Comparative B 7.28 41.12 (0.189,0.388) 6 Example 13 Comparative C 7.22 41.01 (0.188, 0.388) 6 Example 14Example 1 1 7.24 61.88 (0.209, 0.415) 23 Example 2 33 6.98 60.58 (0.224,0.429) 30 Example 3 66 6.89 72.10 (0.243, 0.442) 38 Example 4 78 6.7169.65 (0.205, 0.411) 41 Example 5 101 6.49 71.44 (0.243, 0.442) 39Example 6 152 7.34 58.29 (0.209, 0.419) 30 Example 7 156 7.21 59.33(0.210, 0.420) 29 Example 8 157 7.44 69.65 (0.205, 0.411) 33 Example 9158 7.41 71.44 (0.243, 0.442) 35 Example 10 296 6.95 58.29 (0.209,0.419) 34 Example 11 299 7.21 59.33 (0.210, 0.420) 29 Example 12 3706.71 69.65 (0.205, 0.411) 41 Example 13 372 6.49 71.44 (0.243, 0.442) 39Example 14 373 6.95 58.29 (0.209, 0.419) 34

As seen from the results of Table 17, the organic light emitting deviceusing the charge generation layer material of the 2-stack white organiclight emitting device of the present disclosure had a lower drivingvoltage and improved light emission efficiency compared to ComparativeExample 9 to Comparative Example 11. In addition, compared toComparative Examples 12 to 14, a driving voltage was similar, however,light emission efficiency and lifetime were significantly improved.

Particularly, it can be seen that Compounds B and C of ComparativeExamples 13 and 14 had the core structure of the present applicationsubstituted with one substituent. It was identified that, whensubstituted with one substituent, thermal stability was reduced comparedto the compound substituted with two like the heterocyclic compound ofChemical Formula 1 of the present application, and a lifetime decreasedparticularly.

The invention claimed is:
 1. A heterocyclic compound represented by anyone of the following Chemical Formulae 2 to 9:

wherein, in Chemical Formulae 2 to 9, R₂ to R₅ are the same as ordifferent from each other, and each independently selected from thegroup consisting of hydrogen; or deuterium; Ra is hydrogen; Ar₁ isrepresented by -(L1)p-(Z1)q; Ar₂ is represented by -(L2)r-(Z2)s; L1 is aphenylene group; a biphenylene group; a naphthalene group; a trivalentpyridine group; a trivalent pyrimidine group; or a trivalent triazinegroup; L2 is a phenylene group; a biphenylene group; a naphthalenegroup; a phenanthrenylene group; a triphenylenylene group; afluoranthenylene group; a pyrenylene group; a trivalent pyridine group;a trivalent pyrimidine group; or a trivalent triazine group, Z1 isselected from the group consisting of hydrogen; deuterium; a substitutedor unsubstituted phenyl group; a substituted or unsubstituted biphenylgroup; a substituted or unsubstituted fluorene group; a substituted orunsubstituted pyridine group; a substituted or unsubstituted pyrimidinegroup; a substituted or unsubstituted triazine group; a carbazole group;a dibenzofuran group; a dibenzothiophene group; a substituted orunsubstituted phenanthroline group, —P(═O)RR′; Z2 is selected from thegroup consisting of hydrogen; deuterium; a substituted or unsubstitutedphenyl group; a substituted or unsubstituted biphenyl group; atriphenylene group; a substituted or unsubstituted fluorene group; aphenanthrene group; a substituted or unsubstituted pyridine group; asubstituted or unsubstituted pyrimidine group; a substituted orunsubstituted triazine group; a carbazole group; a dibenzofuran group; adibenzothiophene group; a substituted or unsubstituted phenanthrolinegroup or —P(═O)RR′, R and R′ are the same as or different from eachother, and each independently hydrogen; deuterium; —CN; a substituted orunsubstituted alkyl group; a substituted or unsubstituted cycloalkylgroup; a substituted or unsubstituted aryl group; or a substituted orunsubstituted heteroaryl group; p and r are an integer of 1 to 4; q ands are an integer of 1 to 3; and n is an integer of 0 to
 4. 2. Theheterocyclic compound of claim 1, wherein the “substituted orunsubstituted” means being substituted with one or more substituentsselected from the group consisting of C1 to C60 linear or branchedalkyl; C2 to C60 linear or branched alkenyl; C2 to C60 linear orbranched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 toC60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic orpolycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl;—SiRR′R″; —P(═O)RR′; C1 to C20 alkylamine; C6 to C60 monocyclic orpolycyclic arylamine; and C2 to C60 monocyclic or polycyclicheteroarylamine, or being unsubstituted, or being substituted with asubstituent linking two or more substituents selected from among thesubstituents illustrated above, or being unsubstituted; and R, R′ and R″have the same definitions as in Chemical Formulae 2 to
 9. 3. Theheterocyclic compound of claim 1, wherein Chemical Formulae 2 to 9 arerepresented by any one of the following compounds:


4. An organic light emitting device comprising: a first electrode; asecond electrode provided opposite to the first electrode; and one ormore organic material layers provided between the first electrode andthe second electrode, wherein one or more layers of the organic materiallayers comprise the heterocyclic compound of claim
 1. 5. The organiclight emitting device of claim 4, wherein the organic material layercomprises a light emitting layer, and the light emitting layer comprisesthe heterocyclic compound.
 6. The organic light emitting device of claim4, wherein the organic material layer comprises an electron injectionlayer or an electron transfer layer, and the electron injection layer orthe electron transfer layer comprises the heterocyclic compound.
 7. Theorganic light emitting device of claim 4, wherein the organic materiallayer comprises an electron blocking layer or a hole blocking layer, andthe electron blocking layer or the hole blocking layer comprises theheterocyclic compound.
 8. The organic light emitting device of claim 4,further comprising one, two or more layers selected form the groupconsisting of a light emitting layer, a hole injection layer, a holetransfer layer, an electron injection layer, an electron transfer layer,an electron blocking layer and a hole blocking layer.
 9. The organiclight emitting device of claim 4, comprising: a first electrode; a firststack provided on the first electrode and comprising a first lightemitting layer; a charge generation layer provided on the first stack; asecond stack provided on the charge generation layer and comprising asecond light emitting layer; and a second electrode provided on thesecond stack.
 10. The organic light emitting device of claim 9, whereinthe charge generation layer comprises the heterocyclic compound.
 11. Theorganic light emitting device of claim 9, wherein the charge generationlayer is an N-type charge generation layer, and the charge generationlayer comprises the heterocyclic compound.